Low volatility herbicidal compositions

ABSTRACT

The present invention relates generally low volatility herbicidal compositions comprising at least one auxin herbicide and at least one monocarboxylic acid, or monocarboxylate thereof. The invention further relates generally to methods for preparing and using such low volatility herbicidal compositions, including methods for controlling auxin-susceptible plant growth on agricultural and non-agricultural lands.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a continuation of U.S. application Ser. No. 14/440,789, filedMay 5, 2015, which is a U.S. national stage application of InternationalPatent Application No. PCT/US2013/068507, filed Nov. 5, 2013, whichclaims priority to U.S. Provisional Application Ser. No. 61/794,769filed on Mar. 15, 2013 and U.S. Provisional Application Ser. No.61/722,700 filed on Nov. 5, 2012, the entire disclosures of which areincorporated herein by reference.

FIELD OF THE INVENTION

The present invention relates generally to low volatility herbicidalcompositions comprising at least one auxin herbicide and at least onemonocarboxylic acid, or monocarboxylate thereof. The invention furtherrelates generally to methods for preparing and using such low volatilityherbicidal compositions, including methods for controllingauxin-susceptible plant growth on agricultural and non-agriculturallands.

BACKGROUND OF THE INVENTION

Auxin herbicides, such as dicamba (3,6-dichloro-2-methoxybenzoic acid)and 2,4-D (2,4-dichlorophenoxyacetic acid), are commonly used to controlauxin-susceptible plant growth on both agricultural and non-agriculturallands. Volatility and drift, however, are problems frequently associatedwith these herbicides. Volatile auxin herbicides can, under certainapplication conditions, vaporize into the surrounding atmosphere andmigrate from the application site to adjacent crop plants, such assoybeans and cotton, where contact damage to sensitive plants can occur.Spray drift can be attributed to both volatility and the physicalmovement of small particles from the target site to adjacent cropplants.

Prior approaches to reducing herbicide volatility have included effortsto identify herbicide salts and formulations exhibiting lowervolatility. As one example, the diglycolamine salt of dicamba exhibits alower volatility than the dimethylamine salt of dicamba. Although lowervolatility auxin herbicide salts and formulations have been reported,further reduction in the volatility and off-target movement of auxinherbicides is still desirable.

Another approach to reducing auxin herbicide volatility has focused onencapsulation, for example, absorbing the auxin herbicide into solidphase natural or synthetic polymer, or microencapsulating the auxinherbicide in a polymer shell. Due to technological challenges and otherfactors, however, commercial encapsulation products that satisfactorilyreduce auxin herbicide volatility have not been developed.

Accordingly, auxin herbicide compositions having reduced volatilityrelative to currently available compositions would be desirable,particularly reduced-volatility compositions that exhibit no significantreduction in herbicidal effectiveness relative to currently availablecompositions.

BRIEF DESCRIPTION OF THE INVENTION

In one aspect, the present invention provides herbicidal compositionscomprising at least one auxin herbicide; at least one monocarboxylicacid, or agriculturally acceptable monocarboxylate thereof; and,optionally, a non-auxin herbicide; wherein the compositions exhibitreduced volatility relative to an otherwise identical compositionlacking the monocarboxylic acid or monocarboxylate thereof. In oneembodiment, the auxin herbicide is selected from dicamba, or aagriculturally acceptable salt or ester thereof, and 2,4-D, or anagriculturally acceptable salt of ester thereof. In one embodiment, thecomposition comprises an acetate salt. In another embodiment, thenon-auxin herbicide is glyphosate, or an agriculturally acceptable saltthereof.

In another aspect, the invention provides a herbicidal adjuvantcomposition comprising a monocarboxylic acid, or monocarboxylatethereof, and, optionally, an alkali metal phosphate, that can serve asthe source of monocarboxylic acid, or a monocarboxylate thereof, used inthe preparation of the herbicidal compositions of the present invention.

In another aspect, the invention provides methods of reducing thevolatility of an auxin herbicide, wherein the methods comprise the stepof contacting an auxin herbicide with a volatility-lowering effectiveamount of a monocarboxylic acid, or a monocarboxylate thereof, therebyreducing the volatility of the auxin herbicide.

In another aspect, the invention provides methods of controlling thegrowth of auxin-susceptible plants, wherein the methods compriseapplying to the auxin-susceptible plants a herbicidal compositionapplication mixture comprising at least one auxin herbicide; at leastone monocarboxylic acid, or monocarboxylate thereof; and, optionally, anon-auxin herbicide; wherein the application mixture exhibits reducedauxin herbicide volatility relative to an otherwise identicalapplication mixture lacking the monocarboxylic acid, or monocarboxylatethereof.

In another aspect, the invention provides methods of controllingoff-site movement of an auxin herbicide, wherein the methods comprisecontacting the auxin herbicide with a volatility-lowering effectiveamount of a monocarboxylic acid, or a monocarboxylate thereof, prior toapplication of the auxin herbicide.

In another aspect, the invention provides methods of counseling anindividual regarding the preparation and/or application of an auxinherbicide.

Further benefits of the present invention will be apparent to oneskilled in the art from reading this patent application. The embodimentsof the invention described in the following paragraphs are intended toillustrate the invention and should not be deemed to narrow the scope ofthe invention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides herbicidal compositions comprising anauxin herbicide wherein the compositions exhibit reduced volatilityand/or vapor drift upon application with respect to the auxin herbicide.Specifically, the compositions comprise, in addition to the auxinherbicide, at least one monocarboxylic acid, or monocarboxylate thereof,in an amount sufficient to reduce the volatility of the auxin herbiciderelative to an otherwise identical composition lacking themonocarboxylic acid, or monocarboxylate thereof.

It has been discovered that the addition of a sufficient amount of amonocarboxylic acid, or a monocarboxylate thereof (particularly anon-ammoniated monocarboxylate salt), to a herbicidal compositionconcentrate (e.g., a “premix”) or a herbicidal composition applicationmixture (e.g., a “tank mix”) results in a significant reduction in thelevel of volatile auxin herbicide detected. For some compositions, theamount of volatile auxin herbicide present is actually below thedetection level of sophisticated analytical methods such as liquidchromatography-mass spectrometry (LC/MS). As compared to auxincompositions known in the art, it is believed that the compositions ofthe present invention provide enhanced protection from off-target cropinjury while maintaining comparable herbicidal efficacy onauxin-susceptible plants located in the target area.

The present invention is additionally directed to methods forcontrolling the growth of auxin-susceptible plants, comprising applyingthe herbicidal compositions of the present invention to such plants inaccordance with the guidance provided below.

As used throughout this application, the term “agriculturally acceptablesalt” refers to a salt comprising a cation that is known and accepted inthe art for the formation of salts for agricultural or horticulturaluse. In one embodiment, the salt is a water-soluble salt.

A. AUXIN HERBICIDE COMPONENT

The term “auxin herbicide” refers to a herbicide that functions as amimic of an auxin plant growth hormone, thereby affecting plant growthregulation. Examples of auxin herbicides that are suitable for use inthe herbicidal compositions of the present invention include, withoutlimitation, benzoic acid herbicides, phenoxy herbicides, pyridinecarboxylic acid herbicides, pyridine oxy herbicides, pyrimidine carboxyherbicides, quinoline carboxylic acid herbicides, and benzothiazoleherbicides.

Specific examples of auxin herbicides include:

-   Dicamba (3,6-dichloro-2-methoxy benzoic acid);-   2,4-D (2,4-dichlorophenoxyacetic acid);-   2,4-DB (4-(2,4-dichlorophenoxy)butanoic acid);-   Dichloroprop (2-(2,4-dichlorophenoxy)propanoic acid);-   MCPA ((4-chloro-2-methylphenoxy)acetic acid);-   MCPB (4-(4-chloro-2-methylphenoxy)butanoic acid);-   Aminopyralid (4-amino-3,6-dichloro-2-pyridinecarboxylic acid);-   Clopyralid (3,6-dichloro-2-pyridinecarboxylic acid);-   Fluoroxypyr ([(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic    acid);-   Triclopyr ([(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid);-   Diclopyr;-   Mecoprop (2-(4-chloro-2-methylphenoxy)propanoic acid);-   Mecoprop-P;-   Picloram (4-am ino-3,5,6-trichloro-2-pyridinecarboxylic acid);-   Quinclorac (3,7-dichloro-8-quinolinecarboxylic acid); and-   Aminocyclopyrachlor (6-am    ino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid);

including salts and esters thereof; racemic mixtures and resolvedisomers thereof; and combinations thereof.

In one embodiment, the herbicidal composition comprises dicamba, or anagriculturally acceptable salt or ester thereof. Examples of suitabledicamba salts include the N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine (e.g., BANVEL®, ORACLE®, etc.),isopropylamine, diglycolamine (e.g., CLARITY®, VANQUISH®, etc.),potassium, and sodium salts, and combinations thereof. Commerciallyavailable sources of dicamba, and its agriculturally acceptable salts,include those products sold under the trade names BANVEL®, CLARITY®,DIABLO®, DISTINCT, ORACLE®, VANQUISH®, and VISION®.

In another embodiment, the herbicidal composition comprises anagriculturally acceptable dicamba salt, wherein the salt is selectedfrom the group consisting of N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine,potassium, and sodium salts, and combinations thereof.

Throughout the remainder of the description of the invention, wherereference is made to dicamba, or an agriculturally acceptable salt orester thereof, one skilled in the art will understand that theprinciples of the present invention apply to auxin herbicides generally,including those described above, and that the present invention is notlimited to herbicidal compositions containing dicamba, or anagriculturally acceptable salt or ester thereof.

In another embodiment, the herbicidal composition comprises 2,4-D, or anagriculturally acceptable salt or ester thereof. Examples of suitable2,4-D salts include the choline, dimethylamine, and isopropylaminesalts, and combinations thereof. Examples of suitable 2,4-D estersinclude the methyl, ethyl, propyl, butyl (2,4-DB), and isooctyl esters,and combinations thereof. Commercially available sources of 2,4-D, andits agriculturally acceptable salts and esters, include those productssold under the trade names BARRAGE®, FORMULA 40®, OPT-AMINE®, and WEEDAR64®.

In another embodiment, the herbicidal composition comprises anagriculturally acceptable 2,4-D salt, wherein the salt is selected fromthe group consisting of choline, dimethylamine, and isopropylaminesalts, and combinations thereof.

In another embodiment, the herbicidal composition comprises anagriculturally acceptable 2,4-D ester, wherein the ester is selectedfrom the group consisting of butyl (i.e., 2,4-DB) and isooctyl esters,and combinations thereof.

In another embodiment, the herbicidal composition comprises at least twoauxin herbicides, for example, dicamba, or an agriculturally acceptablesalt or ester thereof, and 2,4-D, or an agriculturally acceptable saltor ester thereof.

In another embodiment, the herbicidal composition comprises anagriculturally acceptable auxin herbicide salt (such as a dicamba salt,a 2,4-D salt, and/or a 2,4-DB salt) that is an ionic liquid as describedin published application US2013/0109572, i.e., a salt that is a liquidat a temperature at or below about 150° C. The entire text ofUS2013/0109572 is incorporated by reference into this application.

B. MONOCARBOXYLIC ACID/MONOCARBOXYLATE COMPONENT

“Monocarboxylic acid” refers to a hydrocarbon or substituted hydrocarboncontaining only one carboxy functional group (i.e., R¹—C(O)OH).“Monocarboxylate” refers to a salt (i.e., R¹—C(O)OM wherein M is anagriculturally acceptable cation) or ester (i.e., R¹—C(O)OR² wherein R²is hydrocarbon or substituted hydrocarbon) of a monocarboxylic acid. Inone embodiment, the composition comprises at least one monocarboxylatesalt, which in aqueous compositions may be present, in whole or in part,in dissociated form as a monocarboxylate anion and the correspondingcation.

Representative monocarboxylic acids and monocarboxylates generallycomprise a hydrocarbon or unsubstituted hydrocarbon selected from, forexample, unsubstituted or substituted, straight or branched chain alkyl(e.g., C₁-C₂₀ alkyl such as methyl, ethyl, n-propyl, isopropyl, etc.);unsubstituted or substituted, straight or branched chain alkenyl (e.g.,C₂-C₂₀ alkyl such as ethenyl, n-propenyl, isopropenyl, etc.);unsubstituted or substituted aryl (e.g., phenyl, hydroxyphenyl, etc.);or unsubstituted or substituted arylalkyl (e.g., benzyl). In oneembodiment, the monocarboxylic acid is selected from the groupconsisting of formic acid, acetic acid, propionic acid, and benzoicacid. In another embodiment, the monocarboxylate salt is selected fromthe group consisting of formate salts, acetate salts, propionate salts,and benzoate salts.

In one embodiment, the herbicidal composition comprises amonocarboxylate salt having the formula R¹—C(O)OM, wherein R¹ isunsubstituted or substituted C₁-C₁₀ alkyl and M is a non-ammoniated,agriculturally acceptable cation. In another embodiment, the herbicidalcomposition comprises a monocarboxylate salt having the formulaR¹—C(O)OM, wherein R¹ is unsubstituted C₁-C₆ alkyl and M is an alkalimetal salt. In another embodiment, the herbicidal composition comprisesa monocarboxylate salt having the formula R¹—C(O)OM, wherein R¹ isunsubstituted C₁-C₃ alkyl and M is an alkali metal salt selected fromsodium and potassium. In another embodiment, the monocarboxylate salt ispotassium acetate. In another embodiment, the monocarboxylate salt issodium acetate.

C. ALKALI METAL PHOSPHATE/ALKALI METAL CARBONATE

The herbicidal compositions of the present invention optionally mayfurther comprise an alkali metal phosphate such as dipotassiumphosphate. Dipotassium phosphate, for example, can provide additionalbuffering and/or water-conditioning for aqueous herbicidal compositionsof the present invention. Dipotassium phosphate is particularlyeffective as a replacement for ammonium sulfate in herbicidalcomposition application mixtures prepared using hard water.

Similarly, the herbicidal compositions of the present inventionoptionally may further comprise an alkali metal carbonate, such aspotassium carbonate, to provide additional buffering and/orwater-conditioning for aqueous herbicidal compositions of the presentinvention.

In some embodiments, the herbicidal compositions of the presentinvention comprise an alkali metal phosphate. In other embodiments, theherbicidal compositions comprise an alkali metal carbonate. In stillother embodiments, the herbicidal compositions comprise an alkali metalphosphate and an alkali metal carbonate.

D. NON-HERBICIDE ADDITIVES

The herbicidal compositions of the present invention optionally mayfurther comprise conventional additives such as surfactants, driftreduction agents, safeners, solubility enhancing agents, thickeningagents, flow enhancers, foam-moderating agents, freeze protectants, UVprotectants, preservatives, antimicrobials, and/or other additives thatare necessary or desirable to improve the performance, crop safety, orhandling of the composition.

In one embodiment, the herbicidal composition comprises less than about10 ppm of ammonium sulfate. In another embodiment, the herbicidalcomposition does not comprise ammonium sulfate.

In one embodiment, the herbicidal composition does not comprise an acidother than a monocarboxylic acid.

E. NON-AUXIN HERBICIDE COMPONENTS

The herbicidal compositions of the present invention optionally mayfurther comprise at least one non-auxin herbicide. The term “non-auxinherbicide” refers to a herbicide having a primary mode of action otherthan as an auxin herbicide. Representative examples of non-auxinherbicides include acetyl CoA carboxylase (ACCase) inhibitors,acetolactate synthase (ALS) inhibitors, acetohydroxy acid synthase(AHAS) inhibitors, photosystem II inhibitors, photosystem I inhibitors,protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoidbiosynthesis inhibitors, enolpyruvyl shikimate-3-phosphate (EPSP)synthase inhibitor, glutamine synthetase inhibitor, dihydropteroatesynthetase inhibitor, mitosis inhibitors, and nucleic acid inhibitors;salts and esters thereof; racemic mixtures and resolved isomers thereof;and combinations thereof.

Representative examples of ACCase inhibitors include clethodim,clodinafop, fenoxaprop-P, fluazifop-P, quizalofop-P, and sethoxydim.

Representative examples of ALS or AHAS inhibitors include flumetsulam,imazamethabenz-m, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,metsulfuron, prosulfuron, and sulfosulfuron.

Representative examples of photosystem I inhibitors include diquat andparaquat.

Representative examples of photosystem II inhibitors include atrazine,cyanazine, diuron, and metibuzin.

Representative examples of PPO inhibitors include acifluorofen,butafenacil, carfentrazone-ethyl, flufenpyr-ethyl, fluthiacet,flumiclorac, flumioxazin, fomesafen, lactofen, oxadiazon, oxyfluorofen,and sulfentrazone.

Representative examples of carotenoid biosynthesis inhibitors includeaclonifen, amitrole, diflufenican, mesotrione, and sulcotrione.

A representative example of an EPSP inhibitor is N-phosphonomethylglycine (glyphosate).

A representative example of a glutamine synthetase inhibitor isglufosinate.

A representative example of a dihydropteroate synthetase inhibitor isasulam.

Representative examples of mitosis inhibitors include acetochlor,alachlor, dithiopyr, S-metolachlor, and thiazopyr.

Representative examples of nucleic acid inhibitors include difenzoquat,fosamine, metham, and pelargonic acid.

In one embodiment, the herbicidal compositions of the present inventionfurther comprise a non-auxin herbicide selected from the groupconsisting of acetochlor, glyphosate, glufosinate, flumioxazin,fomesafen, and agriculturally acceptable salts thereof.

In one embodiment, the herbicidal compositions of the present inventionfurther comprise glyphosate, or an agriculturally acceptable saltthereof. Suitable glyphosate salts include, for example, the ammonium,diammonium, dimethylammonium, monoethanolamine, isopropylamine, andpotassium salts, and combinations thereof. In one embodiment, theglyphosate salts are selected from the group consisting ofmonoethanolamine, isopropylamine, and potassium salts, and combinationsthereof.

In one embodiment, the herbicidal compositions of the present inventionfurther comprise glufosinate, or an agriculturally acceptable saltthereof.

In one embodiment, the herbicidal compositions of the present inventioncomprise dicamba, or an agriculturally acceptable salt or ester thereof,and glyphosate, or an agriculturally acceptable salt thereof. In anotherembodiment, the herbicidal compositions of the present inventioncomprise dicamba, or an agriculturally acceptable salt thereof;glyphosate, or an agriculturally acceptable salt thereof; and anon-ammoniated, agriculturally acceptable acetate salt. Commerciallyavailable sources of glyphosate, and its agriculturally acceptablesalts, include those products sold under the trade names DURANGO® DMA®,HONCHO PLUS®, ROUNDUP POWERMAX®, ROUNDUP WEATHERMAX®, TRAXION®, andTOUCHDOWN®.

In one embodiment, the herbicidal compositions of the present inventioncomprise 2,4-D, or an agriculturally acceptable salt or ester thereof,and glyphosate, or an agriculturally acceptable salt thereof. In anotherembodiment, the herbicidal compositions of the present inventioncomprise 2,4-D, or an agriculturally acceptable salt or ester thereof;glyphosate, or an agriculturally acceptable salt thereof; and anon-ammoniated, agriculturally acceptable acetate salt.

In another embodiment, the herbicidal composition comprises anagriculturally acceptable non-auxin herbicide salt (such as a glyphosatesalt) that is an ionic liquid as described in published applicationUS2013/0109572, i.e., a salt that is a liquid at a temperature at orbelow about 150° C.

F. COMPONENT LOADING

Suitable amounts, concentrations, and/or molar ratios of the auxinherbicide, monocarboxylic acid, or monocarboxylate thereof, and optionalnon-auxin herbicide and non-herbicide additive components of theherbicidal compositions of the present invention will depend to someextent upon whether the composition is a ready-to-use composition, aconcentrate to be diluted with water prior to application (e.g., a“premix”), or a herbicidal composition prepared by combining two or moreherbicide components, water, and, optionally, other non-herbicidecomponents (e.g., a “tank mix”).

1. Herbicide Loading:

Concentrated herbicidal compositions of the present invention typicallycomprise on an acid equivalent basis (a.e.), for example, from about 120to about 600 g a.e./L, from about 300 to about 600 g a.e./L, from about350 to about 600 g a.e./L, from about 400 to about 600 g a.e./L, fromabout 450 to about 600 g a.e./L, or from about 500 to about 600 g a.e./Ltotal herbicide loading. Additional examples of representative totalherbicide loading include about 120, 150, 200, 250, 300, 350, 400, 450,500, 550, and 600 g a.e./L, and ranges thereof (i.e., from about 120 toabout 150 g a.e./L, from about 150 to about 200 g a.e./L, from about 200to about 250 g a.e./L, from about 250 to about 300 g a.e./L, from about300 to about 350 g a.e./L, from about 350 to about 400 g a.e./L fromabout 400 to about 450 g a.e./L, from about 450 to about 500 g a.e./L,from about 500 to about 550 g a.e./L, from about 550 to about 600 ga.e./L total herbicide loading).

In certain embodiments, the herbicidal composition is a liquidconcentrate containing, for example, a total amount (acid equivalentweight) of herbicide from about 5% to about 75% by weight of theconcentrate. In one aspect, the amount is from about 10% to about 60% byweight of the concentrate. In another aspect, the amount is from about15% to about 50% by weight of the concentrate. In another aspect, theamount is from about 20% to about 40% by weight of the concentrate. Inanother aspect, the amount is from about 25% to about 35% by weight ofthe concentrate. In another aspect, the amount is about 30% by weight ofthe concentrate.

In certain embodiments, the herbicidal composition is a dry concentrate(e.g., powder or granules) containing, for example, a total amount (acidequivalent weight) of herbicide from about 40% to about 90% by weight ofthe concentrate. In one aspect, the amount is from about 50% to about80% by weight of the concentrate. In another aspect, the amount is fromabout 60% to about 75% by weight of the concentrate. In another aspect,the amount is from about 65% to about 70% by weight of the concentrate.

Ready-to-use herbicidal compositions and other herbicidal compositionsof the present invention requiring no further processing prior toapplication (e.g., diluted concentrates, tank mixes, etc.) typicallywill comprise on an acid equivalent basis (a.e.) from about 0.1 g a.e./Lto about 50 g a.e./L total herbicide loading. Additional examples ofrepresentative total herbicide loading for such compositions includeabout 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45,and 50 g a.e./L, and ranges thereof (e.g., from about 0.5 to about 5 ga.e./L, from about 5 to about 10 g a.e./L, from about 10 to about 15 ga.e./L, from about 15 to about 20 g a.e./L, from about 20 to about 25 ga.e./L, from about 25 to about 30 g a.e./L from about 30 to about 35 ga.e./L, from about 35 to about 40 g a.e./L, from about 40 to about 45 ga.e./L, from about 45 to about 50 g a.e./L total herbicide loading).

In herbicidal compositions of the present invention comprising an auxinherbicide and a non-auxin herbicide, the weight ratio on an acidequivalent basis of the auxin herbicide to the non-auxin herbicide istypically no greater than about 50:1, for example, about 50:1, 25:1,10:1, 5:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:5, about 1:10, or ranges thereofsuch as from about 50:1 to about 1:10, from about 50:1 to about 1:5,from about 50:1 to about 1:1, from about 50:1 to about 3:1, from about50:1 to about 5:1, from about 50:1 to about 10:1, from about 25:1 toabout 1:1, or from about 25:1 to about 3:1.

For any given auxin herbicide, one skilled in the art can readilydetermine using routine experimentation a minimum concentration of auxinherbicide and a minimum ratio of auxin herbicide to any additional auxinherbicides and/or non-auxin herbicides contained in the herbicidalcomposition that is desirable for the intended application.

2. Monocarboxylic Acid/Monocarboxylate Loading:

As previously noted, it has been discovered that the concentration ofvolatilized auxin herbicide in the vapor phase surrounding a herbicidalcomposition comprising an auxin herbicide and a monocarboxylic acid, ormonocarboxylate thereof, is less than the concentration of volatilizedauxin herbicide in the vapor phase surrounding a reference compositionlacking the monocarboxylic acid or monocarboxylate, but otherwise havingthe same composition. In various embodiments, the concentration ofvolatilized auxin herbicide in the vapor phase surrounding a herbicidalcomposition comprising an auxin herbicide and a monocarboxylic acid, ormonocarboxylate thereof, is less than about 90%, 80%, 70%, 60%, 50%,40%, 30%, 20%, 10%, or 5% A of the concentration of volatilized auxinherbicide in the vapor phase surrounding the reference compositionlacking the monocarboxylate.

The herbicidal compositions of the present invention may comprise asingle monocarboxylic acid, or monocarboxylate thereof, or a mixture oftwo or more monocarboxylic acids, or monocarboxylates thereof.

The monocarboxylic acid or monocarboxylate loading of the herbicidalcomposition generally will depend upon the auxin herbicide loading ofthe herbicidal composition, the salt form of the auxin herbicide, andthe properties of any other components of the herbicidal composition,and will be an amount sufficient to reduce the volatility of the auxinherbicide relative to a reference composition lacking the monocarboxylicacid or monocarboxylate, but otherwise having the same composition. Forexample, the monoethanolamine and diethanolamine salts of dicamba areless volatile than the dimethylamine and isopropylamine salts of dicambaand the loading required for the less volatile salts may be less thanthe loading required for the more volatile salts. In addition, theloading of the monocarboxylic acid, or monocarboxylate thereof, can varywith the specific combination of auxin herbicide, optional non-auxinherbicide, and monocarboxylic acid, or monocarboxylate thereof.

In the herbicidal compositions of the present invention the molar ratioof the auxin herbicide to the monocarboxylic acid, or monocarboxylatethereof, is typically no less than about 1:10 and no greater than about10:1. Representative molar ratios of auxin herbicide acid equivalent(a.e.) to total monocarboxylic acid, or monocarboxylate thereof, are,for example, from 1:10 to about 10:1, from about 1:5 to about 5:1, andfrom about 3:1 to about 1:3. In one aspect, the molar ratio of auxinherbicide to monocarboxylic acid, or monocarboxylate thereof, is about2:1 to about 1:2. In another aspect, the molar ratio of auxin herbicideto monocarboxylic acid, or monocarboxylate thereof, is about 1:1.

In certain embodiments, the herbicidal composition concentrates of thepresent invention contain an amount (acid equivalent weight) of themonocarboxylic acid, or monocarboxylate thereof, from about 0.25% toabout 25% by weight of the concentrate. In one aspect, the amount isfrom about 1% to about 20% by weight of the concentrate. In anotheraspect, the amount is from about 2% to about 15% by weight of theconcentrate. In another aspect, the concentrate is a liquid concentrateand the amount (acid equivalent weight) is from about 2% to about 10% byweight of the concentrate. In another aspect, the concentrate is a dryconcentrate and the amount (acid equivalent weight) is from about 5% toabout 15% by weight of the concentrate. In another aspect, themonocarboxylic acid, or monocarboxylate thereof, is acetic acid, oragriculturally acceptable salt thereof.

In certain embodiments, the herbicidal composition tank mixes of thepresent invention contain an amount (acid equivalent weight) of themonocarboxylic acid, or monocarboxylate thereof, from about 0.01% toabout 25% by weight of the tank mix. In one aspect, the amount is fromabout 0.01% to about 20% by weight of the tank mix. In another aspect,the amount is from about 0.05% to about 15% by weight of the tank mix.In another aspect, the amount is from about 0.05% to about 10% by weightof the tank mix. In another aspect, the amount is from about 0.05% toabout 5% by weight of the tank mix. In another aspect, the amount isfrom about 0.1% to about 2% by weight of the tank mix. In anotheraspect, the amount is from about 0.1% to about 1% by weight of the tankmix. In another aspect, the monocarboxylic acid, or monocarboxylatethereof, is acetic acid, or agriculturally acceptable salt thereof.

3. Alkali Metal Phosphate/Alkali Metal Carbonate Loading

When the herbicidal composition comprises an alkali metal phosphate,such as dipotassium phosphate, the molar ratio of the alkali metalphosphate to the monocarboxylic acid, or monocarboxylate thereof, canrange, for example, from about 1:5 to about 5:1, from about 3:1 to about1:3, or from about 2:1 to about 1:2. In one embodiment, the molar ratioof alkali metal phosphate to monocarboxylic acid, or monocarboxylatethereof, is about 1:1.

When the herbicidal composition comprises an alkali metal carbonate,such as potassium carbonate, the molar ratio of the alkali metalcarbonate to the monocarboxylic acid, or monocarboxylate thereof, canrange, for example, from about 1:5 to about 5:1, from about 3:1 to about1:3, or from about 2:1 to about 1:2. In one embodiment, the molar ratioof alkali metal carbonate to monocarboxylic acid, or monocarboxylatethereof, is about 1:1.

G. HERBICIDAL COMPOSITION EMBODIMENTS

The herbicidal compositions can be presented in various forms dependingupon the intended use and handling properties desired. For example, theherbicidal compositions of the present invention can be prepared in dryform (e.g., powders, granules, etc.) or in liquid form (e.g., aqueoussolutions, dispersions, etc.). The term “aqueous” as used in thisapplication, however, is not intended to exclude the presence ofnon-aqueous (i.e., organic) solvents as long as water is present. Wateris the predominant component of the ready-to-use compositions and tankmix compositions disclosed in this application.

Among the various composition presentations of the invention are thefollowing:

(a) a ready-to-use aqueous herbicidal composition that can be applied tounwanted plants without the need for further dilution with water orother preparation;

(b) a herbicidal composition concentrate that is diluted with water, andoptionally combined with other herbicide and non-herbicide materials,prior to application (including, e.g., dry mixes and premixes);

(c) a herbicidal composition application mixture prepared by diluting aherbicidal composition concentrate with water to form the herbicidalcomposition application mixture which then can be applied toauxin-susceptible plants;

(d) a herbicidal composition application mixture prepared by combiningtwo or more separate components with water (e.g., a tank mix) to formthe herbicidal composition application mixture which then can be appliedto auxin-susceptible plants; and

(e) a herbicidal composition application mixture prepared by introducingseparate feed streams to a spraying or application system so that thefeed streams are co-mixed to form the herbicidal composition applicationmixture immediately prior to use.

In various embodiments, the herbicidal compositions (ready-to-use,liquid concentrate, tank mix, etc.) have a pH that is equal to or higherthan the acid dissociation constant (pKa) of the monocarboxylic acidpresent in the composition. For example, in certain embodiments, theherbicidal compositions comprise acetic acid (which has a pKa of about4.8) and have a pH equal to or greater than about 4.8. In the case ofherbicidal compositions comprising dicamba and an effective amount ofacetic acid, dicamba volatility generally decreases as composition pHincreases with dicamba volatility reaching substantially non-detectablelevels at a composition pH of about 5.2 as measured in a plant responsestudy.

1. Illustrative Composition Embodiments (Auxin Herbicide Concentrates)

One embodiment of the invention is directed to a herbicidal compositionconcentrate comprising:

at least one auxin herbicide; and

at least one monocarboxylic acid, or a monocarboxylate thereof;

wherein the concentrate satisfies one or more of the followingconditions:

the molar ratio of monocarboxylic acid, or monocarboxylate thereof, toauxin herbicide is from about 1:10 to about 10:1;

the acid equivalent weight ratio of monocarboxylic acid, ormonocarboxylate thereof, to auxin herbicide is from about 1:10 to about5:1;

the concentrate contains an amount (acid equivalent weight) of themonocarboxylic acid, or monocarboxylate thereof, from about 0.25% toabout 25% by weight of the concentrate;

the concentration of the monocarboxylic acid, or monocarboxylatethereof, is from about 1 gram (acid equivalent weight)/L to about 250grams (acid equivalent weight)/L; and

the concentrate comprises an amount of the monocarboxylic acid, ormonocarboxylate thereof, sufficient to reduce the concentration ofvolatilized auxin herbicide in the vapor phase surrounding theconcentrate by at least about 10% relative to the concentration ofvolatilized auxin herbicide in the vapor phase surrounding an otherwiseidentical concentrate lacking the monocarboxylic acid, ormonocarboxylate thereof.

In further embodiments, the herbicidal composition concentrate comprisesat least one auxin herbicide selected from the group consisting ofdicamba, or an agriculturally acceptable salt or ester thereof, and2,4-D, or an agriculturally acceptable salt or ester thereof.

In further embodiments, the herbicidal composition concentrate comprisesdicamba, or an agriculturally acceptable salt or ester thereof. Inanother embodiment, the concentrate comprises a dicamba salt selectedfrom the group consisting of N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine,potassium, and sodium salts, and combinations thereof.

In further embodiments, the herbicidal composition concentrate comprises2,4-D, or an agriculturally acceptable salt or ester thereof. In anotherembodiment, the concentrate comprises a 2,4-D salt selected from thegroup consisting of choline, dimethylamine, and isopropylamine salts,and combinations thereof. In another embodiment, the concentratecomprises a 2,4-D ester selected from the group consisting of butyl(i.e., 2,4-DB) and isooctyl esters, and combinations thereof.

In further embodiments, the herbicidal composition concentrate comprisesa monocarboxylate salt.

In further embodiments, the herbicidal composition concentrate comprisesa C₁-C₆-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprises aC₁-C₅-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprises aC₁-C₄-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprises aC₁-C₃-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprisesacetic acid, or an agriculturally acceptable salt thereof. In otherembodiments, the herbicidal composition concentrate comprises formicacid, or an agriculturally acceptable salt thereof.

In further embodiments, the monocarboxylate salt or acetate salt is anon-ammoniated salt. In another embodiment, the monocarboxylate salt oracetate salt is an alkali metal salt. In another embodiment, themonocarboxylate salt or acetate salt is a potassium salt. In anotherembodiment, the monocarboxylate salt or acetate salt is a sodium salt.

In further embodiments, the herbicidal composition concentrate furthercomprises a buffer.

In further embodiments, the herbicidal composition concentrate furthercomprises an alkali metal phosphate, such as dipotassium phosphate.

In further embodiments, the herbicidal composition concentrate is a drypowder herbicidal composition.

In further embodiments, the herbicidal composition concentrate is anaqueous herbicidal composition.

In further embodiments, the herbicidal composition concentrate furthercomprises a non-auxin herbicide. In another embodiment, the non-auxinherbicide is selected from the group consisting of acetochlor,glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturallyacceptable salts thereof. In another embodiment, the non-auxin herbicideis glyphosate, or an agriculturally acceptable salt thereof. In anotherembodiment, the concentrate comprises a glyphosate salt selected fromthe group consisting of ammonium, diammonium, dimethylammonium,monoethanolamine, isopropylamine, and potassium salts, and combinationsthereof. In another embodiment, the concentrate comprising a non-auxinherbicide satisfies one or more of the following conditions:

the sum of the concentration of auxin herbicide and the concentration ofnon-auxin herbicide is from about 120 grams (acid equivalent weight)/Lto about 600 grams (acid equivalent weight)/L;

the acid equivalent weight ratio of auxin herbicide to non-auxinherbicide herbicide is from about 1:5 to about 2:1; and

the acid equivalent weight ratio of monocarboxylic acid, ormonocarboxylate thereof, to auxin herbicide is from about 1:10 to about5:1.

In further embodiments, the herbicidal composition concentrate has a pHgreater than or equal to the pK_(a) of the monocarboxylic acid selectedfor the composition.

2. Illustrative Composition Embodiments (Auxin Herbicide ApplicationMixtures)

One embodiment of the invention is directed to a herbicidal compositioncomprising:

at least one auxin herbicide; and

at least one monocarboxylic acid, or a monocarboxylate thereof;

wherein the composition satisfies one or more of the followingconditions:

the molar ratio of monocarboxylic acid, or monocarboxylate thereof, toauxin herbicide is from about 1:10 to about 10:1;

the acid equivalent weight ratio of monocarboxylic acid, ormonocarboxylate thereof, to auxin herbicide is from about 1:10 to about5:1;

the composition contains an amount (acid equivalent weight) of themonocarboxylic acid, or monocarboxylate thereof, from about 0.01% toabout 25 by weight of the composition;

the concentration of the monocarboxylic acid, or monocarboxylatethereof, is from about 1 gram (acid equivalent weight)/L to about 250grams (acid equivalent weight)/L; and

the composition comprises an amount of the monocarboxylic acid, ormonocarboxylate thereof, sufficient to reduce the concentration ofvolatilized auxin herbicide in the vapor phase surrounding thecomposition by at least about 10% relative to the concentration ofvolatilized auxin herbicide in the vapor phase surrounding an otherwiseidentical composition lacking the monocarboxylic acid, ormonocarboxylate thereof.

In one aspect, the composition contains an amount (acid equivalentweight) of the monocarboxylic acid, or monocarboxylate thereof, fromabout 0.1% to about 25% by weight of the composition.

In further embodiments, the composition comprises at least one auxinherbicide selected from the group consisting of dicamba, or anagriculturally acceptable salt or ester thereof, and 2,4-D, or anagriculturally acceptable salt or ester thereof.

In further embodiments, the composition comprises dicamba, or anagriculturally acceptable salt or ester thereof. In another embodiment,the composition comprises a dicamba salt selected from the groupconsisting of N,N-bis[aminopropyl]methylamine, monoethanolamine,dimethylamine, isopropylamine, diglycolamine, potassium, and sodiumsalts, and combinations thereof.

In further embodiments, the composition comprises 2,4-D, or anagriculturally acceptable salt or ester thereof. In another embodiment,the composition comprises a 2,4-D salt selected from the groupconsisting of choline, dimethylamine, and isopropylamine salts, andcombinations thereof. In another embodiment, the composition comprises a2,4-D ester such as 2,4-DB.

In further embodiments, the composition comprises a monocarboxylatesalt.

In further embodiments, the herbicidal composition concentrate comprisesa C₁-C₆-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprises aC₁-C₅-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprises aC₁-C₄-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprises aC₁-C₃-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the herbicidal composition concentrate comprisesacetic acid, or an agriculturally acceptable salt thereof. In otherembodiments, the herbicidal composition concentrate comprises formicacid, or an agriculturally acceptable salt thereof.

In further embodiments, the monocarboxylate salt or acetate salt is anon-ammoniated salt. In another embodiment, the monocarboxylate salt oracetate salt is an alkali metal salt. In another embodiment, themonocarboxylate salt or acetate salt is a potassium salt. In anotherembodiment, the monocarboxylate salt or acetate salt is a sodium salt.

In further embodiments, the composition further comprises a buffer.

In further embodiments, the herbicidal composition concentrate furthercomprises an alkali metal phosphate, such as dipotassium phosphate.

In further embodiments, the composition is an aqueous herbicidalcomposition.

In further embodiments, the composition further comprises a non-auxinherbicide. In another embodiment, the non-auxin herbicide is selectedfrom the group consisting of acetochlor, glyphosate, glufosinate,flumioxazin, fomesafen, and agriculturally acceptable salts thereof. Inanother embodiment, the non-auxin herbicide is glyphosate, or anagriculturally acceptable salt thereof. In another embodiment, theconcentrate comprises a glyphosate salt selected from the groupconsisting of ammonium, diammonium, dimethylammonium, monoethanolamine,isopropylamine, and potassium salts, and combinations thereof. Inanother embodiment, the concentrate comprising a non-auxin herbicidesatisfies one or more of the following conditions:

the sum of the concentration of auxin herbicide and the concentration ofnon-auxin herbicide is from about 1 gram (acid equivalent weight)/L toabout 50 grams (acid equivalent weight)/L;

the acid equivalent weight ratio of auxin herbicide to non-auxinherbicide is from about 1:5 to about 2:1; and

the acid equivalent weight ratio of monocarboxylic acid, ormonocarboxylate thereof, to auxin herbicide is from about 1:10 to about5:1.

3. Illustrative Composition Embodiments (Dicamba Concentrate)

Compositions of particular interest include herbicidal compositionscomprising dicamba, or an agriculturally acceptable salt or esterthereof; acetic acid, or an agriculturally acceptable salt thereof; and,optionally, glyphosate, or an agriculturally acceptable salt thereof.

One embodiment of the invention is directed to a herbicidal compositionconcentrate comprising:

dicamba, or an agriculturally acceptable salt or ester thereof; and

acetic acid, or an agriculturally acceptable salt thereof;

wherein the molar ratio of acetic acid, or agriculturally acceptablesalt thereof, to dicamba, or agriculturally acceptable salt or esterthereof, is from about 1:10 to about 10:1.

In another embodiment, the herbicidal composition concentrate comprises:

(a) dicamba, or an agriculturally acceptable salt or ester thereof; and

(b) acetic acid, or an agriculturally acceptable salt thereof;

wherein the acid equivalent weight ratio of acetic acid, oragriculturally acceptable salt thereof, to dicamba, or agriculturallyacceptable salt or ester thereof, is from about 1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate comprises:

(a) dicamba, or an agriculturally acceptable salt or ester thereof; and

(b) acetic acid, or an agriculturally acceptable salt thereof;

wherein the concentrate contains an amount (acid equivalent weight) ofthe acetic acid, or agriculturally acceptable salt thereof, from about0.25% to about 25% by weight of the concentrate.

In another embodiment, the herbicidal composition concentrate comprises:

(a) dicamba, or an agriculturally acceptable salt or ester thereof; and

(b) acetic acid, or an agriculturally acceptable salt thereof;

wherein the concentration of the acetic acid, or agriculturallyacceptable salt thereof, is from about 1 gram (acid equivalent weight)/Lto about 250 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate comprises:

(a) dicamba, or an agriculturally acceptable salt or ester thereof; and

(b) acetic acid, or an agriculturally acceptable salt thereof;

wherein the concentration of dicamba, or an agriculturally acceptablesalt or ester thereof, is from about 120 grams (acid equivalentweight)/L to about 600 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate comprises:

(a) dicamba, or an agriculturally acceptable salt or ester thereof; and

(b) acetic acid, or an agriculturally acceptable salt thereof;

wherein the concentration of dicamba, or an agriculturally acceptablesalt or ester thereof, is from about 120 grams (acid equivalentweight)/L to about 600 grams (acid equivalent weight)/L; and

wherein the acid equivalent weight ratio of acetic acid, oragriculturally acceptable salt thereof, to dicamba, or agriculturallyacceptable salt or ester thereof, is from about 1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate comprises:

(a) dicamba, or an agriculturally acceptable salt or ester thereof; and

(b) acetic acid, or an agriculturally acceptable salt thereof;

wherein the concentrate comprises an amount of the acetic acid, oragriculturally acceptable salt thereof, sufficient to reduce theconcentration of volatilized dicamba, or agriculturally acceptable saltor ester thereof, in the vapor phase surrounding the concentrate by atleast about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% Arelative to the concentration of volatilized dicamba, or agriculturallyacceptable salt or ester thereof, in the vapor phase surrounding anotherwise identical concentrate lacking the acetic acid, oragriculturally acceptable salt thereof.

In further embodiments, the herbicidal composition concentrate comprisesa dicamba salt selected from the group consisting ofN,N-bis-[aminopropyl]methylamine, monoethanolamine, dim ethylamine,isopropylamine, diglycolamine, potassium, and sodium salts, andcombinations thereof.

In further embodiments, the herbicidal composition concentrate comprisesan acetate salt. In another embodiment, the acetate salt is an alkalimetal salt. In another embodiment, the acetate salt is a potassium salt.In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the herbicidal composition concentrate furthercomprises a buffer.

In further embodiments, the herbicidal composition concentrate furthercomprises an alkali metal phosphate, such as dipotassium phosphate.

In further embodiments, the herbicidal composition concentrate is a drypowder herbicidal composition.

In further embodiments, the herbicidal composition concentrate is anaqueous herbicidal composition.

In further embodiments, the herbicidal composition concentrate furthercomprises a non-auxin herbicide. In another embodiment, the non-auxinherbicide is selected from the group consisting of acetochlor,glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturallyacceptable salts thereof. In another embodiment, the concentratecomprising a non-auxin herbicide satisfies one or more of the followingconditions:

the sum of the concentration of auxin herbicide and the concentration ofnon-auxin herbicide is from about 120 grams (acid equivalent weight)/Lto about 600 grams (acid equivalent weight)/L;

the acid equivalent weight ratio of auxin herbicide to non-auxinherbicide is from about 1:5 to about 2:1; and

the acid equivalent weight ratio of monocarboxylic acid, ormonocarboxylate thereof, to auxin herbicide is from about 1:10 to about5:1.

In further embodiments, the herbicidal composition concentrate has a pHgreater than or equal to the pK_(a) of acetic acid (i.e., 4.8).

4. Illustrative Composition Embodiments (Dicamba/Glyphosate Concentrate)

One embodiment of the invention is directed to a herbicidal compositionconcentrate comprising:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the molar ratio of acetic acid, or agriculturally        acceptable salt thereof, to dicamba, or agriculturally        acceptable salt or ester thereof, is from about 1:10 to about        10:1.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the acid equivalent weight ratio of acetic acid, or        agriculturally acceptable salt thereof, to dicamba, or        agriculturally acceptable salt or ester thereof, is from about        1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the concentrate contains an amount (acid equivalent        weight) of the acetic acid, or agriculturally acceptable salt        thereof, from about 0.25% to about 25% by weight of the        concentrate.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the concentration of the acetic acid, or agriculturally        acceptable salt thereof, is from about 1 gram (acid equivalent        weight)/L to about 250 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the sum of the concentration of dicamba, or an        agriculturally acceptable salt or ester thereof, and the        concentration of glyphosate, or an agriculturally acceptable        salt thereof, is from about 120 grams (acid equivalent weight)/L        to about 600 grams (acid equivalent weight)/L. In another        embodiment, the sum of the concentration of dicamba, or an        agriculturally acceptable salt or ester thereof, and the        concentration of glyphosate, or an agriculturally acceptable        salt thereof, is from about 360 grams (acid equivalent weight)/L        to about 480 grams (acid equivalent weight)/L.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the sum of the concentration of dicamba, or an        agriculturally acceptable salt or ester thereof, and the        concentration of glyphosate, or an agriculturally acceptable        salt thereof, is from about 120 grams (acid equivalent weight)/L        to about 600 grams (acid equivalent weight)/L; and    -   wherein the acid equivalent weight ratio of dicamba, or an        agriculturally acceptable salt or ester thereof, to glyphosate,        or an agriculturally acceptable salt thereof, is from about 1:5        to about 2:1.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the sum of the concentration of dicamba, or an        agriculturally acceptable salt or ester thereof, and the        concentration of glyphosate, or an agriculturally acceptable        salt thereof, is from about 120 grams (acid equivalent weight)/L        to about 600 grams (acid equivalent weight)/L;    -   wherein the acid equivalent weight ratio of dicamba, or an        agriculturally acceptable salt or ester thereof, to glyphosate,        or an agriculturally acceptable salt thereof, is from about 1:5        to about 2:1; and    -   wherein the acid equivalent weight ratio of acetic acid, or        agriculturally acceptable salt thereof, to dicamba, or        agriculturally acceptable salt or ester thereof, is from about        1:10 to about 5:1.

In another embodiment, the herbicidal composition concentrate comprises:

-   -   (a) dicamba, or an agriculturally acceptable salt or ester        thereof;    -   (b) glyphosate, or an agriculturally acceptable salt thereof;        and    -   (c) acetic acid, or an agriculturally acceptable salt thereof;    -   wherein the concentrate comprises an amount of the acetic acid,        or agriculturally acceptable salt thereof, sufficient to reduce        the concentration of volatilized dicamba, or agriculturally        acceptable salt or ester thereof, in the vapor phase surrounding        the concentrate by at least about 10%, 20%, 30%, 40%, 50%, 60%,        70%, 80%, 90%, or 95% A relative to the concentration of        volatilized dicamba, or agriculturally acceptable salt or ester        thereof, in the vapor phase surrounding an otherwise identical        concentrate lacking the acetic acid, or agriculturally        acceptable salt thereof.

In further embodiments, the herbicidal composition concentrate comprisesa dicamba salt selected from the group consisting ofN,N-bis-[aminopropyl]methylamine, monoethanolamine, dimethylamine,isopropylamine, diglycolamine, potassium, and sodium salts, andcombinations thereof.

In further embodiments, the herbicidal composition concentrate comprisesan acetate salt. In another embodiment, the acetate salt is an alkalimetal salt. In another embodiment, the acetate salt is a potassium salt.In another embodiment, the acetate salt is a sodium salt.

In further embodiments, the herbicidal composition concentrate furthercomprises a buffer.

In further embodiments, the herbicidal composition concentrate furthercomprises an alkali metal phosphate, such as dipotassium phosphate.

In further embodiments, the herbicidal composition concentrate is a drypowder herbicidal composition.

In further embodiments, the herbicidal composition concentrate is anaqueous herbicidal composition.

In another embodiment, the concentrate comprises a glyphosate saltselected from the group consisting of ammonium, diammonium,dimethylammonium, monoethanolamine, isopropylamine, and potassium salts,and combinations thereof.

In another embodiment, the concentrate satisfies one or more of thefollowing conditions:

-   -   the sum of the concentration of dicamba, or agriculturally        acceptable salt thereof, and the concentration of glyphosate, or        agriculturally acceptable salt thereof, is from about 120 grams        (acid equivalent weight)/L to about 600 grams (acid equivalent        weight)/L;    -   the acid equivalent weight ratio of dicamba, or agriculturally        acceptable salt thereof, to glyphosate, or agriculturally        acceptable salt thereof, is from about 1:5 to about 2:1; and    -   the acid equivalent weight ratio of monocarboxylic acid, or        monocarboxylate thereof, to dicamba, or agriculturally        acceptable salt thereof, is from about 1:10 to about 5:1.

In further embodiments, the herbicidal composition concentrate has a pHgreater than or equal to the pK_(a) of acetic acid (i.e., 4.8).

5. Illustrative Composition Embodiments (Dicamba Application Mixture)

In further embodiments, the herbicidal compositions correspond to thecompositions described above in the “Illustrative Composition Embodiment(Auxin Herbicide Application Mixture)” section wherein the auxinherbicide is dicamba, or an agriculturally acceptable salt or esterthereof.

6. Illustrative Composition Embodiments (Dicamba/Glyphosate ApplicationMixture)

In further embodiments, the herbicidal compositions correspond to thecompositions described above in the “Illustrative Composition Embodiment(Auxin Herbicide Application Mixture)” section wherein the auxinherbicide is dicamba, or an agriculturally acceptable salt or esterthereof, and the compositions further comprise glyphosate, or anagriculturally acceptable salt or ester thereof.

7. Illustrative Composition Embodiments (Dicamba/Glufosinate ApplicationMixture)

In further embodiments, the herbicidal compositions correspond to thecompositions described above in the “Illustrative Composition Embodiment(Auxin Herbicide Application Mixture)” section wherein the auxinherbicide is dicamba, or an agriculturally acceptable salt or esterthereof, and the compositions further comprise glufosinate, or anagriculturally acceptable salt or ester thereof.

8. Illustrative Composition Embodiments (2,4-D)

Compositions of particular interest also include herbicidal compositionscomprising 2,4-D, or an agriculturally acceptable salt or ester thereof;acetic acid, or an agriculturally acceptable salt thereof; and,optionally, glyphosate, or an agriculturally acceptable salt thereof.

In further embodiments, the herbicidal compositions correspond to thecompositions described above in the “Illustrative Composition Embodiment(Dicamba Concentrate),” “Illustrative Composition Embodiment(Dicamba/Glyphosate Concentrate),” “Illustrative Composition Embodiment(Dicamba Application Mixture),” “Illustrative Composition Embodiment(Dicamba/Glyphosate Application Mixture)” and “Illustrative CompositionEmbodiment (Dicamba/Glufosinate Application Mixture)” sections exceptthat the dicamba, or agriculturally acceptable salt or ester thereof, isreplaced with 2,4-D, or an agriculturally acceptable salt or esterthereof.

9. Illustrative Composition Embodiments (Dicamba Liquid Concentrate)

One embodiment of the invention is directed to a herbicidal compositionthat is a liquid concentrate comprising:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 1% to about 25% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 10% to about 60% by weight of the concentrate.

In one aspect, the liquid concentrate has a dicamba loading from about300 g a.e./L to about 400 g a.e./L.

In another embodiment, the liquid concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 2% to about 20% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 15% to about 50% by weight of the concentrate.

In another embodiment, the liquid concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 3% to about 15% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 20% to about 40% by weight of the concentrate.

In another embodiment, the liquid concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 3% to about 10% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 25% to about 35% by weight of the concentrate.

In further embodiments, the liquid concentrate comprises a dicamba saltselected from the group consisting of N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine,potassium, and sodium salts, and combinations thereof. In one aspect,the liquid concentrate comprises a dicamba diglycolamine salt.

In further embodiments, the liquid concentrate comprises an acetatesalt. In another embodiment, the acetate salt is an alkali metal salt.In another embodiment, the acetate salt is a potassium salt. In anotherembodiment, the acetate salt is a sodium salt.

In further embodiments, the liquid concentrate comprises an acetate saltthat is formed in situ during the preparation of the liquid concentratewhen acetic acid is contacted with a neutralizing base such as an alkalimetal hydroxide. For example, the liquid concentrate can be prepared bymixing the dicamba, or agriculturally acceptable salt or ester thereof,with water followed by the addition of acetic acid followed by theaddition of the neutralizing base. Although a specific order of additionof the ingredients is not required to prepare the final composition, theorder of addition described above can be advantageous to reduce the heatgeneration resulting when the ingredients are combined. In one aspect,the neutralizing base is potassium hydroxide. In another aspect, theneutralizing base is sodium hydroxide.

10. Illustrative Composition Embodiments (Dicamba Dry Concentrate)

One embodiment of the invention is directed to a herbicidal compositionthat is a dry concentrate comprising:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 1% to about 40% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 40% to about 90% by weight of the concentrate; and    -   wherein the sum of the acetic acid weight percent and the        dicamba weight percent is less than or equal to 100%.

In another embodiment, the dry concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 3% to about 30% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 50% to about 80% by weight of the concentrate; and    -   wherein the sum of the acetic acid weight percent and the        dicamba weight percent is less than or equal to 100%.

In another embodiment, the dry concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 5% to about 20% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 60% to about 75% by weight of the concentrate.

In further embodiments, the dry concentrate comprises a dicamba saltselected from the group consisting of N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine,potassium, and sodium salts, and combinations thereof. In one aspect,the liquid concentrate comprises a dicamba diglycolamine salt.

In further embodiments, the dry concentrate comprises an acetate salt.In another embodiment, the acetate salt is an alkali metal salt. Inanother embodiment, the acetate salt is a potassium salt. In anotherembodiment, the acetate salt is a sodium salt.

In further embodiments, the dry concentrate is in the form of a drypowder.

In further embodiments, the dry concentrate is in the form of drygranules.

11. Illustrative Composition Embodiments (Dicamba/Glyphosate LiquidPremix)

One embodiment of the invention is directed to a herbicidal compositionthat is a liquid concentrate comprising:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 1% to about 25% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 2% to about 25% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 4% to about 50% by weight of the concentrate.

In one aspect, the liquid concentrate has a total herbicide loading fromabout 350 g a.e./L to about 500 g a.e./L.

In another embodiment, the liquid concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 2% to about 20% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 3% to about 20% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 6% to about 40% by weight of the concentrate.

In another embodiment, the liquid concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 3% to about 15% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 4% to about 15% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 8% to about 30% by weight of the concentrate.

In another embodiment, the liquid concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 3% to about 10% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 5% to about 15% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 10% to about 30% by weight of the concentrate.

In further embodiments, the liquid concentrate comprises a dicamba saltselected from the group consisting of N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine,potassium, and sodium salts, and combinations thereof. In one aspect,the liquid concentrate comprises a dicamba diglycolamine salt.

In further embodiments, the liquid concentrate comprises an acetatesalt. In another embodiment, the acetate salt is an alkali metal salt.In another embodiment, the acetate salt is a potassium salt. In anotherembodiment, the acetate salt is a sodium salt.

In further embodiments, the liquid concentrate comprises an acetate saltthat is formed in situ during the preparation of the liquid concentratewhen acetic acid is contacted with a neutralizing base such as an alkalimetal hydroxide. For example, the liquid concentrate can be prepared bymixing the dicamba, or agriculturally acceptable salt or ester thereof,with water followed by the addition of acetic acid followed by theaddition of the neutralizing base. Although a specific order of additionof the ingredients is not required to prepare the final composition, theorder of addition described above can be advantageous to reduce the heatgeneration resulting when the ingredients are combined. In one aspect,the neutralizing base is potassium hydroxide. In another aspect, theneutralizing base is sodium hydroxide.

12. Illustrative Composition Embodiments (Dicamba/Glyphosate Dry Premix)

One embodiment of the invention is directed to a herbicidal compositionthat is a dry concentrate comprising:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 1% to about 40% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 5% to about 40% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 40% to about 80% by weight of the concentrate; and    -   wherein the sum of the acetic acid weight percent, the dicamba        weight percent, and the glyphosate weight percent is less than        or equal to 100%.

In another embodiment, the dry concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 3% to about 30% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 10% to about 35% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 40% to about 70% by weight of the concentrate; and    -   wherein the sum of the acetic acid weight percent, the dicamba        weight percent, and the glyphosate weight percent is less than        or equal to 100%.

In another embodiment, the dry concentrate comprises:

-   -   dicamba, or an agriculturally acceptable salt or ester thereof;        and    -   glyphosate, or an agriculturally acceptable salt thereof; and    -   acetic acid, or an agriculturally acceptable salt thereof;    -   wherein:    -   the concentrate contains an amount (acid equivalent weight) of        the acetic acid, or agriculturally acceptable salt thereof, from        about 5% to about 15% by weight of the concentrate;    -   the concentrate contains an amount (acid equivalent weight) of        dicamba, or an agriculturally acceptable salt or ester thereof,        from about 20% to about 30% by weight of the concentrate; and    -   the concentrate contains an amount (acid equivalent weight) of        glyphosate, or an agriculturally acceptable salt thereof, from        about 45% to about 55% by weight of the concentrate.

In further embodiments, the dry concentrate comprises a dicamba saltselected from the group consisting of N,N-bis-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine,potassium, and sodium salts, and combinations thereof. In one aspect,the liquid concentrate comprises a dicamba diglycolamine salt.

In further embodiments, the dry concentrate comprises an acetate salt.In another embodiment, the acetate salt is an alkali metal salt. Inanother embodiment, the acetate salt is a potassium salt. In anotherembodiment, the acetate salt is a sodium salt.

In further embodiments, the dry concentrate is in the form of a drypowder.

In further embodiments, the dry concentrate is in the form of drygranules.

13. Illustrative Composition Embodiments (Combination Package)

One embodiment of the invention is directed to a combination packagecomprising a first container comprising dicamba, or an agriculturallyacceptable salt or ester thereof; and a second container comprisingacetic acid, or an agriculturally acceptable salt thereof. In oneaspect, the first container comprises dicamba, or an agriculturallyacceptable salt or ester thereof, in an amount (acid equivalent weight)that is at least about 20% by weight of the first container. In oneaspect, the first container contains a liquid composition comprisingdicamba, or an agriculturally acceptable salt or ester thereof. In oneaspect, the first container contains a dry composition comprisingdicamba, or an agriculturally acceptable salt or ester thereof.

In another embodiment, the invention is directed to a combinationpackage comprising a first container comprising dicamba, or anagriculturally acceptable salt or ester thereof; a second containercomprising glyphosate, or an agriculturally acceptable salt thereof; anda third container comprising acetic acid, or an agriculturallyacceptable salt thereof. In one aspect, the first container comprisesdicamba, or an agriculturally acceptable salt or ester thereof, in anamount (acid equivalent weight) that is at least about 20% by weight ofthe first container. In one aspect, the first container contains aliquid composition comprising dicamba, or an agriculturally acceptablesalt or ester thereof. In one aspect, the first container contains a drycomposition comprising dicamba, or an agriculturally acceptable salt orester thereof. In one aspect, the second container comprises glyphosate,or an agriculturally acceptable salt thereof, in an amount (acidequivalent weight) that is at least about 20% by weight of the secondcontainer. In one aspect, the second container contains a liquidcomposition comprising glyphosate, or an agriculturally acceptable saltthereof. In one aspect, the second container contains a dry compositioncomprising glyphosate, or an agriculturally acceptable salt thereof.

In another embodiment, the invention is directed to a combinationpackage comprising a first container comprising dicamba, or anagriculturally acceptable salt or ester thereof; a second containercomprising glufosinate, or an agriculturally acceptable salt or esterthereof; and a third container comprising acetic acid, or anagriculturally acceptable salt thereof. In one aspect, the firstcontainer comprises dicamba, or an agriculturally acceptable salt orester thereof, in an amount (acid equivalent weight) that is at leastabout 20% by weight of the first container. In one aspect, the firstcontainer contains a liquid composition comprising dicamba, or anagriculturally acceptable salt or ester thereof. In one aspect, thefirst container contains a dry composition comprising dicamba, or anagriculturally acceptable salt or ester thereof. In one aspect, thesecond container comprises glufosinate, or an agriculturally acceptablesalt or ester thereof, in an amount (acid equivalent weight) that is atleast about 10% by weight of the second container. In one aspect, thesecond container contains a liquid composition comprising glufosinate,or an agriculturally acceptable salt or ester thereof. In one aspect,the second container contains a dry composition comprising glufosinate,or an agriculturally acceptable salt or ester thereof.

In another embodiment of the invention is directed to a combinationpackage comprising a first container comprising glyphosate, or anagriculturally acceptable salt thereof; and a second containercomprising acetic acid, or an agriculturally acceptable salt thereof. Inone aspect, the first container comprises glyphosate, or anagriculturally acceptable salt thereof, in an amount (acid equivalentweight) that is at least about 20% by weight of the first container. Inone aspect, the first container contains a liquid composition comprisingglyphosate, or an agriculturally acceptable salt thereof. In one aspect,the first container contains a dry composition comprising glyphosate, oran agriculturally acceptable salt thereof.

In another embodiment of the invention is directed to a combinationpackage comprising a first container comprising glufosinate, or anagriculturally acceptable salt or ester thereof; and a second containercomprising acetic acid, or an agriculturally acceptable salt thereof. Inone aspect, the first container comprises glufosinate, or anagriculturally acceptable salt thereof, in an amount (acid equivalentweight) that is at least about 10% by weight of the first container. Inone aspect, the first container contains a liquid composition comprisingglufosinate, or an agriculturally acceptable salt thereof. In oneaspect, the first container contains a dry composition comprisingglufosinate, or an agriculturally acceptable salt thereof.

H. HERBICIDAL COMPOSITION ADJUVANT

As discussed in more detail later, in certain embodiments the methods ofcontrolling the growth of auxin-susceptible plants involve thepreparation of an application mixture by combining a source of auxinherbicide (e.g., CLARITY®); a source of monocarboxylic acid, or amonocarboxylate thereof; an optional source of non-auxin herbicide(e.g., DURANGO® or POWERMAX®); and water. Another embodiment of thepresent invention, therefore, is directed to a herbicidal adjuvantcomposition comprising a monocarboxylic acid, or monocarboxylatethereof, and, optionally, an alkali metal phosphate, that can serve asthe source of monocarboxylic acid, or a monocarboxylate thereof, used inthe preparation of the application mixture.

In one embodiment, the adjuvant composition for use in the preparationof the herbicidal composition application mixture comprises:

-   -   (a) at least one monocarboxylic acid, or a monocarboxylate        thereof; and    -   (b) an alkali metal phosphate;    -   wherein the molar ratio of monocarboxylic acid, or        monocarboxylate thereof, to alkali metal phosphate is from about        1:5 to about 5:1.

In various embodiments, the adjuvant composition comprises aC₁-C₆-alkanoic acid, or an agriculturally acceptable salt thereof. Inother embodiments, the adjuvant composition comprises a C₁-C₅-alkanoicacid, or an agriculturally acceptable salt thereof. In otherembodiments, the adjuvant composition comprises a C₁-C₄-alkanoic acid,or an agriculturally acceptable salt thereof. In other embodiments, theadjuvant composition comprises a C₁-C₃-alkanoic acid, or anagriculturally acceptable salt thereof. In other embodiments, theadjuvant composition comprises a monocarboxylic acid is selected fromthe group consisting of formic acid, acetic acid, propionic acid, andbenzoic acid. In other embodiments, the adjuvant composition comprisesacetic acid, or an agriculturally acceptable salt thereof. In otherembodiments, the adjuvant composition comprises formic acid, or anagriculturally acceptable salt thereof.

In another embodiment, the adjuvant composition for use in thepreparation of the herbicidal composition application mixture comprises:

-   -   (a) at least one monocarboxylic acid, or a monocarboxylate        thereof; and    -   (b) an alkali metal phosphate;    -   wherein the molar ratio of monocarboxylic acid, or        monocarboxylate thereof, to alkali metal phosphate is from about        1:5 to about 5:1; and    -   wherein the composition contains an amount (acid equivalent        weight) of the monocarboxylic acid, or monocarboxylate thereof,        from about 2% to about 40% by weight of the composition.

In another embodiment, the adjuvant composition for use in thepreparation of the aqueous herbicidal application mixture comprises:

-   (a) acetic acid, or an agriculturally acceptable salt thereof; and-   (b) an alkali metal phosphate;-   wherein the molar ratio of acetic acid, or agriculturally acceptable    salt thereof, to alkali metal phosphate is from about 1:5 to about    5:1.

In another embodiment, the adjuvant composition for use in thepreparation of the aqueous herbicidal application mixture comprises:

-   -   (a) acetic acid, or an agriculturally acceptable salt thereof;        and    -   (b) an alkali metal phosphate;    -   wherein the molar ratio of acetic acid, or agriculturally        acceptable salt thereof, to alkali metal phosphate is from about        1:5 to about 5:1; and    -   wherein the composition contains an amount (acid equivalent        weight) of the acetic acid, or agriculturally acceptable salt        thereof, from about 2% to about 40% by weight of the        composition.

In another embodiment, the invention relates to an adjuvant compositionfor use in the preparation of the aqueous herbicidal applicationmixture, wherein the adjuvant composition comprises acetic acid, or anagriculturally acceptable salt thereof, in an amount (acid equivalentweight) of about 2% to about 75% by weight of the composition. In oneaspect, the amount is from about 10% to about 75% by weight of thecomposition. In another aspect, the amount is from about 20% to about75% by weight of the composition. In another aspect, the amount is fromabout 30% to about 75% by weight of the composition.

In various embodiments of the adjuvant composition, the composition is adry powder composition.

In various embodiments of the adjuvant composition, the composition is aliquid composition, particularly an aqueous composition.

In various embodiments of the adjuvant composition, the compositioncomprises a non-ammoniated monocarboxylate or acetate salt. In otherembodiments, the salt is an alkali metal salt, such as an alkali metalsalt. In other embodiments, the salt is a potassium salt or a sodiumsalt, such as potassium acetate and sodium acetate.

In various embodiments of the adjuvant composition, the alkali metalphosphate is dipotassium phosphate.

In various embodiments of the adjuvant composition, the compositioncomprises potassium acetate and dipotassium phosphate.

I. METHODS OF REDUCING THE VOLATILITY OF AN AUXIN HERBICIDE

Another embodiment of the present invention is directed to a method ofreducing the volatility of an auxin herbicide. The method generallycomprises the step of contacting an auxin herbicide with avolatility-lowering effective amount of a monocarboxylic acid, or amonocarboxylate thereof, thereby reducing the volatility of the auxinherbicide.

In one embodiment, the contacting step satisfies at least one of thefollowing conditions:

-   -   the molar ratio of the monocarboxylic acid, or monocarboxylate        thereof, contacted with the auxin herbicide is from about 1:10        to about 10:1;    -   the acid equivalent weight ratio of the monocarboxylic acid, or        monocarboxylate thereof, contacted with the auxin herbicide is        from about 1:10 to about 5:1; and    -   the amount of the monocarboxylic acid, or monocarboxylate        thereof, contacted with the auxin herbicide is sufficient to        reduce the concentration of volatilized auxin herbicide in the        vapor phase by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%,        80%, 90%, or 95% relative to the concentration of volatilized        auxin herbicide in the vapor phase for an auxin herbicide in the        absence of the monocarboxylic acid, or monocarboxylate thereof.

Volatilization can be measured by conventional means known to thoseskilled in the art. In one such method, for example, a gas stream ispassed over an auxin herbicide composition and the auxin herbicidevolatilizes from the composition into the gas stream which is thenquantitatively analyzed for auxin herbicide content by methods known inthe art. In another method, an auxin herbicide composition is distilledand the distillation condensate and/or distilled composition is analyzedfor auxin herbicide content. In still another method, auxin herbicidevolatilization is qualitatively assessed in a plant response study on achosen sensitive species which will be clear to one of skill in the art.

It is believed that the addition of the monocarboxylic acid, ormonocarboxylate thereof, at the loading values discussed above to theherbicidal compositions of the present invention effectively reducesauxin herbicide volatility and the associated crop injury withoutsignificantly reducing auxin herbicide effectiveness.

In one embodiment, no reduction in auxin herbicide effectiveness isobserved for a herbicidal composition of the present invention relativeto a reference composition lacking the monocarboxylic acid, ormonocarboxylate thereof, but otherwise having the same composition.

In another embodiment, the auxin herbicide effectiveness of a herbicidalcomposition of the present invention is at least about 80%, 85%, 90%,95%, or 99% of the auxin herbicide effectiveness of a referencecomposition lacking the monocarboxylic acid, or monocarboxylate thereof,but otherwise having the same composition.

In another embodiment, a reduced rate of crop injury is observed for aherbicidal composition of the present invention relative to a referencecomposition lacking the monocarboxylic acid, or monocarboxylate thereof,but otherwise having the same composition.

In another embodiment, the rate of crop injury associated with aherbicidal composition of the present invention is less than about 90%,80%, 70%, 60%, or 50% of the crop injury associated with a referencecomposition lacking the monocarboxylic acid, or monocarboxylate thereof,but otherwise having the same composition.

In another embodiment, a reduction in the rate of crop injury and noreduction in auxin herbicide effectiveness are observed for theherbicidal compositions of the present invention relative to a referencecomposition lacking the monocarboxylic acid, or monocarboxylate thereof,but otherwise having the same composition.

In another embodiment, the herbicidal composition loading of themonocarboxylic acid, or monocarboxylate thereof, is sufficient toprovide both commercially acceptable weed control and a commerciallyacceptable rate of crop injury.

A “commercially acceptable rate of weed control” varies with the weedspecies, degree of infestation, environmental conditions, and theassociated crop plant. Typically, commercially effective weed control isdefined as least about 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or evengreater than 95%. Although it is generally preferable from a commercialviewpoint that 80 to 85% or more of the weeds be destroyed, commerciallysignificant weed control can occur at much lower levels, particularlywith some very noxious, herbicide-resistant plants. “Weed control,” asused herein, refers to any observable measure of control of plantgrowth, which can include one or more of the actions of (1) killing, (2)inhibiting growth, reproduction or proliferation, and (3) removing,destroying, or otherwise diminishing the occurrence and activity ofplants. Weed control can be measured by any of the various methods knownin the art. For example, weed control can be determined as a percentageas compared to untreated plants following a standard procedure wherein avisual assessment of plant mortality and growth reduction is made by oneskilled in the art specially trained to make such assessments. Inanother control measurement method, control is defined as an averageplant weight reduction percentage between treated and untreated plants.Preferably, commercial weed control is achieved at no greater than 30days after treatment (DAT), such as from 18 to 30 DAT.

A “commercially acceptable rate of crop injury” for the presentinvention likewise varies with the crop plant species. Typically, acommercially acceptable rate of crop injury is defined less than about20%, 15%, 10% or even less than about 5%. Crop damage can be measured byany means known in the art, such as those describe above for weedcontrol determination. Preferably, crop damage appears no more than from10% to 20% at no greater than 30 DAT, such as from 3 to 21 or from 3 to30 DAT.

J. METHODS OF CONTROLLING GROWTH OF AUXIN-SUSCEPTIBLE PLANTS

Another embodiment of the present invention is directed to methods ofcontrolling the growth of auxin-susceptible plants, particularly thosegrowing in and/or adjacent to a field of crop plants. The methodsgenerally comprise applying to the auxin-susceptible plants an aqueousherbicidal composition mixture comprising at least one auxin herbicide;at least one monocarboxylic acid, or monocarboxylate thereof; and,optionally, a non-auxin herbicide; wherein the application mixtureexhibits reduced auxin herbicide volatility relative to an otherwiseidentical application mixture lacking the monocarboxylic acid, ormonocarboxylate thereof.

The aqueous herbicidal composition mixture applied to theauxin-susceptible plants can be provided, for example, in the followingmanner:

-   -   (a) as a ready-to-use aqueous herbicidal composition that can be        applied without the need for further dilution with water or        other preparation;    -   (b) as a herbicidal composition application mixture prepared by        diluting with water any of the herbicidal composition        concentrates within in the scope of the present disclosure;    -   (c) as a herbicidal composition application mixture prepared by        combining two or more separate components with water (e.g., a        tank mix);    -   (d) as a herbicidal composition application mixture prepared by        introducing separate feed streams to a spraying or application        system so that the feed streams are co-mixed immediately prior        to use; or    -   (e) in any other manner reasonably adapted to apply to        auxin-susceptible plants a herbicidal composition comprising the        auxin herbicide in admixture with the monocarboxylic acid, or        monocarboxylate thereof.

In one embodiment, the methods of controlling the growth ofauxin-susceptible plants comprise the steps of:

-   -   (a) preparing an aqueous herbicidal application mixture by        diluting with water a herbicidal composition concentrate of any        of the herbicidal composition concentrates disclosed in this        application; and    -   (b) applying a herbicidally effective amount of the application        mixture to the auxin-susceptible plants.

In another embodiment, the preparing step does not comprise separatelyintroducing a pH-lowering agent (e.g., an acidifying agent) with theconcentrate and water during the preparation of the application mixture;wherein the pH-lowering agent is one that is capable of lowering the pHof the application mixture in the absence of any buffering provided byother components of the application mixture.

In one embodiment, the methods of controlling the growth ofauxin-susceptible plants comprise the steps of:

-   -   (a) combining a source of auxin herbicide; a source of        monocarboxylic acid, or a monocarboxylate thereof; and water to        prepare an aqueous herbicidal application mixture; and    -   (b) applying a herbicidally effective amount of the application        mixture to the auxin-susceptible plants;    -   wherein the application mixture satisfies one or more of the        following conditions:    -   the molar ratio of monocarboxylic acid, or monocarboxylate        thereof, to auxin herbicide is from about 1:10 to about 10:1;    -   the acid equivalent weight ratio of monocarboxylic acid, or        monocarboxylate thereof, to auxin herbicide is from about 1:10        to about 5:1;    -   the application mixture contains an amount (acid equivalent        weight) of the monocarboxylic acid, or monocarboxylate thereof,        from about 0.01% to about 25 by weight of the application        mixture;    -   the concentration of the monocarboxylic acid, or monocarboxylate        thereof, is from about 1 gram (acid equivalent weight)/L to        about 250 grams (acid equivalent weight)/L; and    -   the application mixture comprises an amount of the        monocarboxylic acid, or monocarboxylate thereof, sufficient to        reduce the concentration of volatilized auxin herbicide in the        vapor phase surrounding the application mixture by at least        about 10% relative to the concentration of volatilized auxin        herbicide in the vapor phase surrounding an otherwise identical        application mixture lacking the monocarboxylic acid, or        monocarboxylate thereof.

In one aspect, the application mixture contains an amount (acidequivalent weight) of the monocarboxylic acid, or monocarboxylatethereof, from about 0.1% to about 25%, by weight of the applicationmixture.

In another embodiment, the methods of controlling the growth ofauxin-susceptible plants comprise the steps of:

-   -   (a) combining a source of auxin herbicide; a source of non-auxin        herbicide, or agriculturally acceptable salt thereof; a source        of monocarboxylic acid, or a monocarboxylate thereof; and water        to prepare an aqueous herbicidal application mixture; and    -   (b) applying a herbicidally effective amount of the application        mixture to the auxin-susceptible plants;    -   wherein the application mixture satisfies one or more of the        following conditions:    -   the molar ratio of monocarboxylic acid, or monocarboxylate        thereof, to auxin herbicide is from about 1:10 to about 10:1;    -   the acid equivalent weight ratio of monocarboxylic acid, or        monocarboxylate thereof, to auxin herbicide is from about 1:10        to about 5:1;    -   the application mixture contains an amount (acid equivalent        weight) of the monocarboxylic acid, or monocarboxylate thereof,        from about 0.01% to about 25 by weight of the application        mixture;    -   the concentration of the monocarboxylic acid, or monocarboxylate        thereof, is from about 1 gram (acid equivalent weight)/L to        about 250 grams (acid equivalent weight)/L; and    -   the application mixture comprises an amount of the        monocarboxylic acid, or monocarboxylate thereof, sufficient to        reduce the concentration of volatilized auxin herbicide in the        vapor phase surrounding the application mixture by at least        about 10% relative to the concentration of volatilized auxin        herbicide in the vapor phase surrounding an otherwise identical        application mixture lacking the monocarboxylic acid, or        monocarboxylate thereof.

In one aspect, the application mixture contains an amount (acidequivalent weight) of the monocarboxylic acid, or monocarboxylatethereof, from about 0.1% to about 25%, by weight of the applicationmixture.

When the methods of controlling the growth of auxin-susceptible plantsinvolve the use of a herbicidal composition application mixturecomprising a non-auxin herbicide, the application mixture generallysatisfies one or more of the following conditions:

-   -   the sum of the concentration of auxin herbicide and the        concentration of non-auxin herbicide is from about 1 gram (acid        equivalent weight)/L to about 50 grams (acid equivalent        weight)/L;    -   the acid equivalent weight ratio of auxin herbicide to non-auxin        herbicide is from about 1:5 to about 2:1; and    -   the acid equivalent weight ratio of monocarboxylic acid, or        monocarboxylate thereof, to auxin herbicide is from about 1:10        to about 5:1.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the application mixture comprises anon-auxin herbicide is selected from the group consisting of acetochlor,glyphosate, glufosinate, flumioxazin, fomesafen, and agriculturallyacceptable salts thereof. In one embodiment, the application mixturecomprises glyphosate, or an agriculturally acceptable salt thereof. Inanother embodiment, the application mixture comprises glufosinate, or anagriculturally acceptable salt thereof.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the auxin herbicide is selected fromthe group consisting of dicamba, or an agriculturally acceptable salt orester thereof, and 2,4-D, or an agriculturally acceptable salt or esterthereof.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the auxin herbicide is dicamba, oran agriculturally acceptable salt or ester thereof.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the auxin herbicide is 2,4-D, or anagriculturally acceptable salt or ester thereof.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the application mixture comprises amonocarboxylate salt.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the application mixture comprisesacetic acid, or an agriculturally acceptable salt thereof.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the monocarboxylate or acetate saltis a non-ammoniated salt. In still other embodiments, the salt is analkali metal salt. In still other embodiments, the salt is a potassiumsalt. In still other embodiments, the salt is a sodium salt.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the application mixture furthercomprises a buffer.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the application mixture furthercomprises an alkali metal phosphate, such as dipotassium phosphate.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants, the combining step does not compriseseparately introducing a pH-lowering agent with the source of auxinherbicide; the source of monocarboxylic acid, or monocarboxylatethereof; and water during the preparation of the application mixture;wherein the pH-lowering agent is one that is capable of lowering the pHof the application mixture in the absence of any buffering provided byother components of the application mixture.

In various embodiments of the described methods of controlling thegrowth of auxin-susceptible plants wherein the application mixturecomprises a non-auxin herbicide, the combining step does not compriseseparately introducing a pH-lowering agent with the source of auxinherbicide; the source of non-auxin herbicide; the source ofmonocarboxylic acid, or monocarboxylate thereof; and water during thepreparation of the application mixture; wherein the pH-lowering agent isone that is capable of lowering the pH of the application mixture in theabsence of any buffering provided by other components of the applicationmixture.

In the described methods, the application mixture is applied to theauxin-susceptible plants at an application rate sufficient to give acommercially acceptable rate of weed control. The appropriateapplication rate for the application mixture can be readily determinedby one of skill in the art and is usually expressed as amount of auxinherbicide per unit area treated, e.g., grams acid equivalent per hectare(g a.e./ha). Depending on the plant species and growing conditions, theperiod of time required to achieve a commercially acceptable rate ofweed control can be as short as a week or as long as three weeks, fourweeks, or one month. Typically, a period of about two to three weeks isneeded for the auxin herbicide to exert its full effect.

The timing of application can vary. The application mixture can beapplied, for example, pre-planting of the crop plant, such as from abouttwo to about three weeks before planting auxin-susceptible crop plantsor crop plants not having a auxin herbicide-resistant trait. Crop plantsthat are not susceptible to certain auxin herbicides (such as corn orplants having an auxin herbicide-resistant trait), however, generallyhave no pre-planting restriction and the application mixture can beapplied immediately before planting such crops.

The auxin-susceptible plants can be weeds or crop plants. Crop plantsinclude, for example, vegetable crops, grain crops, flowers, and rootcrops. Crop plants further encompass hybrids, inbreds, and transgenic orgenetically modified plants.

In some embodiments, the crop plants are auxin tolerant species that arenot susceptible to auxin herbicides or are a transgenic species thatcontain an auxin (e.g., dicamba) resistant trait. Examples includedicamba resistant corn, cotton or soybean. Dicamba resistant crops canfurther comprise one or more additional traits including, withoutlimitation: herbicide resistance (e.g., resistance to other auxinherbicides (e.g., 2,4-D or fluoroxypyr), glyphosate, glufosinate,acetolactate synthase inhibitor herbicides (e.g., imazamox, imazethapyr,imazaquin and imazapic), acetyl CoA carboxylase inhibitors (e.g.,sethoxydim and clethodim), etc.); insect resistance such as Bacillusthuringiensis (Bt); high oil; high lysine; high starch; nutritionaldensity; and/or drought resistance.

In some embodiments, the weeds and/or crop plants are glyphosatetolerant or contain a glyphosate resistant trait. Examples includeglyphosate resistant corn, cotton or soybean.

In some embodiments, the crop plants comprise stacked traits such asdicamba and glyphosate resistance; dicamba and glufosinate resistance;dicamba and acetolactate synthase (ALS) or acetohydroxy acid synthase(AHAS) resistance; dicamba, glyphosate and glufosinate resistance;dicamba, glyphosate and ALS or AHAS resistance; dicamba, glufosinate andALS or AHAS resistance; or dicamba, glyphosate, glufosinate and ALS orAHAS resistance.

In some embodiments, the plants can additionally include otherherbicide, insect and disease resistance traits, as well as combinationsof those traits. For instance, the plants can have dicamba, 2,4-D, orfluoroxypyr resistant traits.

K. METHODS OF CONTROLLING OFF-SITE MOVEMENT

Another embodiment of the present invention is directed to a method ofcontrolling off-site movement of an auxin herbicide by contacting theauxin herbicide with a volatility-lowering effective amount of amonocarboxylic acid, or a monocarboxylate thereof, prior to applicationof the auxin herbicide.

In one embodiment, the method comprises the steps of:

-   -   (a) preparing an aqueous herbicidal application mixture        comprising an auxin herbicide; a monocarboxylic acid, or a        monocarboxylate thereof; water; and, optionally, a source of        non-auxin herbicide; and    -   (b) applying a herbicidally effective amount of the application        mixture to auxin-susceptible plants;    -   wherein the application mixture satisfies one or more of the        following conditions:    -   the molar ratio of monocarboxylic acid, or monocarboxylate        thereof, to auxin herbicide is from about 1:10 to about 10:1;    -   the acid equivalent weight ratio of monocarboxylic acid, or        monocarboxylate thereof, to auxin herbicide is from about 1:10        to about 5:1;    -   the application mixture contains an amount (acid equivalent        weight) of the monocarboxylic acid, or monocarboxylate thereof,        from about 0.01% to about 25 by weight of the application        mixture;    -   the concentration of the monocarboxylic acid, or monocarboxylate        thereof, is from about 1 gram (acid equivalent weight)/L to        about 250 grams (acid equivalent weight)/L; and    -   the application mixture comprises an amount of the        monocarboxylic acid, or monocarboxylate thereof, sufficient to        reduce the concentration of volatilized auxin herbicide in the        vapor phase surrounding the application mixture by at least        about 10% relative to the concentration of volatilized auxin        herbicide in the vapor phase surrounding an otherwise identical        application mixture lacking the monocarboxylic acid, or        monocarboxylate thereof.

In one aspect, the application mixture contains an amount (acidequivalent weight) of the monocarboxylic acid, or monocarboxylatethereof, from about 0.1% to about 25%, by weight of the applicationmixture.

L. METHODS OF COUNSELING ON USE OF AN AUXIN HERBICIDE

Another embodiment of the present invention is directed to methods ofcounseling an individual regarding the preparation and/or application ofan auxin herbicide.

In one embodiment, the invention is directed to a method of counselingan individual on the application of an auxin herbicide toauxin-susceptible plants, the method comprising:

-   -   (a) identifying a source of an auxin herbicide;    -   (b) instructing the individual to prepare an aqueous herbicidal        composition application mixture from the source of auxin        herbicide; and    -   (c) additionally instructing the individual to supplement the        application mixture with a monocarboxylic acid, or        monocarboxylate thereof, prior to the application of the        application mixture to auxin-susceptible plants.

In another embodiment, the invention is directed to a method ofcounseling an individual on the application of an auxin herbicide toauxin-susceptible plants, the method comprising:

-   -   (a) identifying a source of an auxin herbicide;    -   (b) identifying a source of a monocarboxylic acid, or a        monocarboxylate thereof; and    -   (c) instructing the individual to prepare an aqueous herbicidal        composition application mixture from the source of auxin        herbicide and the source of monocarboxylic acid, or        monocarboxylate thereof, for application to the        auxin-susceptible plants.

The source of monocarboxylic acid, or a monocarboxylate thereof, can be,for example, a single source such as the herbicidal composition adjuvantpreviously discussed, or even a source that provides for in situformation of the monocarboxylic acid, or monocarboxylate thereof, in theherbicidal composition application mixture.

Having described the invention in detail, it will be apparent thatmodifications and variations are possible without departing from thescope of the invention defined in the appended claims.

M. EXAMPLES

The following non-limiting examples are provided to further illustratethe present invention. It should be noted that the composition examplesbelow are presented on the basis of the components initially combined toform the reported tank mix or concentrate. The various embodiments ofthe present invention are intended to encompass such initialcompositions as well as any corresponding compositions resulting frominteraction among the components once combined, such as where amonocarboxylic acid salt is formed in situ by combining a monocarboxylicacid with a neutralizing base.

Example 1-A: Tank Mix Compositions (Dicamba+Glyphosate)

Unless otherwise specified, the herbicidal tank mix compositionsdisclosed in Examples 1-A, 1-B, and 1-C were prepared using CLARITY®(DGA dicamba from BASF), ROUNDUP POWERMAX® (potassium glyphosate fromMonsanto), BANVEL® (DMA dicamba from BASF), DURANGO® DMA® (DMAglyphosate from Dow AgroSciences), LIBERTY® (ammonium glufosinate fromBayer CropScience), and/or 2,4-D amine (Albaugh) by successively addingeach specified herbicide to water and mixing. Those tank mixformulations containing additional tank mix adjuvants such as potassiumacetate (Sigma), dipotassium phosphate (ICL), and/or ammonium sulfate(Sigma) were typically prepared by adding aqueous stock solutions of theadjuvants to the herbicide mixture.

Herbicide salts not purchased from a commercial vendor, such as IPAglyphosate and MEA dicamba, typically were prepared by mixing theherbicide acid with the desired amine. The herbicide acid to amine ratiotypically is about 1:1. In certain instances, a slight excess of amineis desired. As used in these examples, DGA refers to diglycolamine; DMArefers to dimethylamine; IPA refers to isopropylamine; and MEA refers tomonoethanolamine.

Herbicidal tank mix compositions prepared by the method described aboveare listed in Tables 1-1 through 1-15 below:

TABLE 1-1 (Composition 854-B) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 30.00 3.00% 1.20% ae ROUNDUP POWERMAX ® 60.60 6.06%2.40% ae water 909.78

TABLE 1-2 (Composition 854-C) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 30.03 3.00% 1.20% ae ROUNDUP POWERMAX ® 60.34 6.03%2.40% ae dipotassium phosphate (50%) 40.02 4.00% 2.00% water 869.74

TABLE 1-3 (Composition 854-F) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 7.50 3.00% 1.20% ae ROUNDUP POWERMAX ® 15.14 6.06%2.40% ae potassium acetate 5.04 2.01% 2.01% Water 222.42

TABLE 1-4 (Composition 751-E) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 7.51 3.00% 1.20% ae ROUNDUP POWERMAX ® 15.16 6.06%2.40% ae ammonium sulfate (AMS) 7.35 2.94% 1.00% water 220.07

TABLE 1-5 (Composition 751-D) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 7.49 3.00% 1.20% ae ROUNDUP POWERMAX ® 15.10 6.06%2.40% ae potassium acetate (50%) 10.00 4.00% 2.00% ammonium sulfate(34%) 7.34 2.94% 1.00% water 210.07

TABLE 1-6 (Composition 210-D) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 7.48 3.00% 1.20% ae ROUNDUP POWERMAX ® 14.99 6.00%2.40% ae 1:1 wt/wt 50% potassium acetate/ 10.00 4.00% 2.00% 50%dipotassium phosphate water 217.42

TABLE 1-7 (Composition 870-A) INGREDIENT WT (g) WT % % ACTIVE DMAglyphosate 15.04 6.02% 2.40% ae (DURANGO ® DMA ®) 2,4-D amine 15.506.20% 2.40% ae water 219.54

TABLE 1-8 (Composition 870-B) INGREDIENT WT (g) WT % % ACTIVE DMAglyphosate 15.04 6.02% 2.40% ae (DURANGO ® DMA ®) 2,4-D amine 15.436.17% 2.40% ae potassium acetate (50%) 10.02 4.00% 2.00% water 209.57

TABLE 1-9 (Composition 870-C) INGREDIENT WT (g) WT % % ACTIVE IPAglyphosate (30.8% ae) 19.54 7.82% 2.40% ae 2,4-D amine 15.42 6.17% 2.40%ae potassium acetate (50%) 10.00 4.00% 2.00% water 205.04

TABLE 1-10 (Composition 870-D) INGREDIENT WT (g) WT % % ACTIVE IPAglyphosate (30.8%) 19.54 7.82 2.40% ae 2,4-D amine 15.42 6.17 2.40% aewater 215.04

TABLE 1-11 (Composition 563-2) INGREDIENT WT (g) WT % % ACTIVE BANVEL ®7.34 2.94% 1.20% ae ROUNDUP POWERMAX ® 15.00 6.00% 2.40% ae water 227.66

TABLE 1-12 (Composition 563-5) INGREDIENT WT (g) WT % % ACTIVE BANVEL ®7.34 2.94% 1.20% ae ROUNDUP POWERMAX ® 15.07 6.00% 2.40% ae potassiumacetate (50%) 10.05 4.00% 2.00% water 217.65

TABLE 1-13 (Composition 563-1) INGREDIENT WT (g) WT % % ACTIVE MEAdicamba (62.2%) 4.81 1.93% 1.20% ae ROUNDUP POWERMAX ® 15.00 6.00% 2.40%ae water 230.18

TABLE 1-14 (Composition 563-4) INGREDIENT WT (g) WT % % ACTIVE MEAdicamba (62.2%) 4.85 1.93% 1.20% ae ROUNDUP POWERMAX ® 14.96 6.00 2.40%ae potassium acetate (50%) 10.03 4.00%   2% water 220.18

TABLE 1-15 (Composition 836-1) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®6.01 3.0 1.2% ae ROUNDUP POWERMAX ® 12.05 6.1 2.4% ae water 181.98

For the tank mix compositions in Table 1-16 through Table 1-19, themonocarboxylic acid salt (e.g., potassium acetate) was formed in situ bycombining a monocarboxylic acid with a neutralizing base. Thecompositions were prepared by mixing the herbicide(s) with waterfollowed by addition of the monocarboxylic acid followed by addition ofthe neutralizing base. Although a specific order of addition of theingredients is not required to prepare the final composition, the orderof addition described above can be advantageous to reduce the heatgeneration resulting when the ingredients are combined. The neutralizingbase (potassium hydroxide in the compositions below) was added as a 45%w/w aqueous solution.

TABLE 1-16 (Composition 836-2) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®6.00 3.0 1.2% ae ROUNDUP POWERMAX ® 12.04 6.0 2.4% ae succinic acid 2.571.3 potassium hydroxide (45% solution) 5.46 water 174.01

TABLE 1-17 (Composition 836-3) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®6.00 3.0 1.2% ae ROUNDUP POWERMAX ® 12.09 6.0 2.4% ae propionic acid1.63 0.8 potassium hydroxide (45% solution) 2.72 water 177.65

TABLE 1-18 (Composition 836-4) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®6.01 3.0 1.2% ae ROUNDUP POWERMAX ® 12.03 6.0 2.4% ae acetic acid 1.320.7 potassium hydroxide (45% solution) 2.73 water 177.98

TABLE 1-19 (Composition 836-5) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®6.05 3.0 1.2% ae ROUNDUP POWERMAX ® 12.03 6.0 2.4% ae formic acid 1.000.5 potassium hydroxide (45% solution) 2.73 Water 178.32

TABLE 1-20 (Composition 836-6) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®6.01 3.0 1.2% ae ROUNDUP POWERMAX ® 12.03 6.0 2.4% ae potassiumhydroxide (45% solution) 1.78 0.9 water 180.19

TABLE 1-21 (Composition 893-A) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.50 3.0 1.2% ae ROUNDUP POWERMAX ® 15.20 6.0 2.4% ae water 227.46

TABLE 1-22 (Composition 893-B) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.50 3.0 1.2% ae ROUNDUP POWERMAX ® 15.04 6.0 2.4% ae potassium acetate(50% solution) 10.04 2.0% ai water 217.44

TABLE 1-23 (Composition 893-C) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.67 3.0 1.2% ae ROUNDUP POWERMAX ® 15.02 6.0 2.4% ae potassium formate5.05 2.0% ai water 222.46

TABLE 1-24 (Composition 893-D) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.51 3.0 1.2% ae ROUNDUP POWERMAX ® 15.03 6.0 2.4% ae potassium benzoate5.05 2.0% ai water 222.45

TABLE 1-25 (Composition 893-F) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.51 3.0 1.2% ae ROUNDUP POWERMAX ® 15.04 6.0 2.4% ae sodium acetate5.01 2.0% ai  water 222.44

TABLE 1-26 (Composition 854-A) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®30.0 3.0 1.2% ae water

TABLE 1-27 (Composition 854-D) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.5 3.0 1.2 ae ROUNDUP POWERMAX ® 15.08 6.0 2.4 ae potassium oxalate(25% solution) 20.0 8.0 2.0 ai  water 207.42

TABLE 1-28 (Composition 854-E) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®7.5 3.0 1.2 ae ROUNDUP POWERMAX ® 15.08 6.0 2.4 ae potassium citrate(50%) 10.0 4.0 water 217.42

TABLE 1-29 (Composition 268-1) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.13 3.05 1.20 ae ammonium glyphosate (ROUNDUP ®7.10 3.53 2.40 ae ENERGY) water 186.78 93.422 * ROUNDUP ® ENERGY is theglyphosate ammonium salt, sold as water soluble granules in Europe.

TABLE 1-30 (Composition 268-2) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.09 3.05 1.20 ae ammonium glyphosate (ROUNDUP ®7.09 3.53 2.40 ae ENERGY) dipotassium phosphate 9.12 4.56 3.00 water177.72 88.86

TABLE 1-31 (Composition 268-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.09 3.05 1.20 ae ammonium glyphosate (ROUNDUP ®7.10 3.53 2.40 ae ENERGY) potassium acetate 7.99 4.00 4.00 water 178.7889.42

TABLE 1-32 (Composition 268-4) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.25 3.05 1.20 ae ammonium glyphosate (ROUNDUP ®7.09 3.53 2.40 ae ENERGY) potassium acetate 8.00 16.01 4.00 water 170.8185.42

TABLE 1-33 (Composition 268-5) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.09 3.05 1.20 ae ammonium glyphosate (ROUNDUP ®7.07 3.53 2.40 ae ENERGY) potassium acetate 8.02 4.00 2.00 dipotassiumphosphate 9.08 4.56 3.00 water 169.69 84.86

TABLE 1-34 (Composition 268-6) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.11 3.05 1.20 ae ROUNDUP POWERMAX ® 12.00 6.00 2.40ae water 181.90 90.95

Example 1-B: Tank Mix Compositions (Dicamba+Glufosinate)

TABLE 1-35 (Composition 364-2) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.04 6.04  1.2% ae ammonium glufosinate (LIBERTY ®)7.59 7.59 3.36% v/v water 186.57 186.57

TABLE 1-36 (Composition 364-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.05 6.05  1.2% ae ammonium glufosinate (LIBERTY ®)7.41 7.41 3.36% v/v dipotassium phosphate (50%) 9.19 9.19 3.00% v/vwater 177.40 177.40

TABLE 1-37 (Composition 364-5) INGREDIENT WT % % ACTIVE DGA dicamba(CLARITY ®) 2.9  1.2% ae potassium hydroxide 0.38 acetic acid 0.23ammonium glufosinate (LIBERTY ®) 3.7 3.36% v/v water 92.79

TABLE 1-38 (Composition 364-6) INGREDIENT WT % % ACTIVE DGA dicamba(CLARITY ®) 2.9  1.2% ae potassium hydroxide 0.38 acetic acid 0.23ammonium glufosinate (LIBERTY ®) 3.7 3.36% v/v dipotassium phosphate 4.63.00% v/v water 88.19

Example 1-C: Tank Mix Compositions (Dicamba)

TABLE 1-39 (Composition 364-1) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 6.00 6.00 1.20% ae water 194.00 194.00

TABLE 1-40 (Composition 364-4) INGREDIENT WT % % ACTIVE DGA dicamba(CLARITY ®) 2.9 1.2% ae potassium hydroxide 0.38 acetic acid 0.23 water96.45

The compositions shown in Tables 1-37, 1-38, and 1-40 above(Compositions 364-5, 364-6, and 364-4, respectively) were prepared bycombining the appropriate amount of the composition shown in Table 2-17below (Composition 871-5) with the additional components and an amountof water sufficient to provide a final dicamba concentration of 1.2% ae.

Example 1-D: Acetic Acid Adjuvant

An example of an acetic acid adjuvant for use in the preparation of adicamba tank mix is described in Table 1-41 below.

TABLE 1-41 Adjuvant (Composition 828-2) INGREDIENT WT (g) WT % potassiumacetate 25.04 25.0 potassium citrate (monohydrate) 24.98 25.0 water50.02 50.0 total 100.04 100.0

Example 2-A: Liquid Concentrate Compositions (Dicamba)

Liquid concentrate compositions are described in Examples 2-A, 2-B, 2-C,and 2-D.

The potassium acetate used in the compositions in Tables 2A-1-29 throughTable 2A-1-32 was prepared by adding the desired amount of glacialacetic acid to the desired amount of potassium hydroxide (45% w/wsolution) in an ice bath without allowing the temperature of thesolution to rise above 60° C. The pre-formed potassium acetate was thenadded to the solution containing the herbicide(s). The ratio indicatedin the tables below is on a molar basis. For example, “50/50 AcOH/KOH”means a 1:1 M ratio of acetic acid to potassium hydroxide. Thecompositions in the tables below were prepared by adding the desiredamount of each ingredient and stirring for about 20 minutes.

Alternatively, the monocarboxylic acid salt can be prepared by addingthe monocarboxylic acid to the solution containing the herbicide(s)followed by addition of a neutralizing base. Although a specific orderof addition of the ingredients is not required to prepare the finalcomposition, the order of addition described above can be advantageousto reduce the heat generation resulting when the ingredients arecombined.

TABLE 2A-1-29 (Composition 503-1) INGREDIENT WT (g) WT % % ACTIVECLARITY ® 157.4 78.7 31.0 50/50 AcOH/KOH 42.6 21.3 6.9 (AcOH)

TABLE 2A-1-30 (Composition 503-3) INGREDIENT WT (g) WT % % ACTIVECLARITY ® 157.4 78.7 31.0 60/40 AcOH/KOH 42.6 21.3 8.2 (AcOH)

TABLE 2A-1-31 (Composition 295-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 112.3 56.2 31.0 60/40 AcOH/KOH 65.1 32.6 12.6 (AcOH)water 22.6 11.3

TABLE 2A-1-32 (Composition 295-6) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 112.3 56.2 31.0 60/40 AcOH/KOH 86.8 43.4 16.8 (AcOH)water 0.9 0.4

TABLE 2A-1-33 (Composition 771-C) INGREDIENT WT (g) WT % % ACTIVECLARITY ® 29.15 62.94 acetic acid 6.26 6.26 potassium hydroxide 8.728.72 water 2.19 2.19

TABLE 2A-1-34 (Composition 761-B) INGREDIENT WT (g) WT % % ACTIVECLARITY ® 32.82 71.20 acetic acid 4.48 9.72 potassium hydroxide 6.2413.53 water 2.56

Example 2-B: Liquid Concentrate Compositions (Dicamba+Glyphosate)

Herbicidal compositions containing DGA dicamba and MEA glyphosate wereprepared by mixing CLARITY® with MEA glyphosate with water. Afterstirring the mixture for five minutes, surfactants AGM550 and AgniquePG8107-G were added followed by ferric citrate (for mitigating necrosisin certain crops) and anti-foaming agent SAG 1572, and the mixturestirred for an additional 30 minutes. Premix compositions which alsocontain additional adjuvants, such as potassium acetate, were preparedas described above with the modification of replacing the water with thedesired amount of aqueous adjuvant. The MEA glyphosate salt used in thepreparation of the compositions was prepared by mixing glyphosate acidand 1.35 molar equivalents of MEA with water. The list of ingredients ofthe dicamba/glyphosate premix composition is set forth in Table 2-1.

TABLE 2-1 (DGA Dicamba/MEA Glyphosate Premix) INGREDIENT WT (g) WT % %ACTIVE DGA dicamba (CLARITY ®) 32.36 32.36% 12.75% 1.35 MEA glyphosate(46.9%) 54.37 54.37% 25.50% AGM 550 2.50 2.50% Agnique PG8107-G 5.005.00% SAG 1572 0.01 0.01% Ferric citrate (7.0% Fe) 0.31 0.31% 0.02%water 5.44 5.44%

Dicamba/glyphosate premixes containing additional adjuvants, such aspotassium acetate, typically were prepared by adding the desired amountof an aqueous solution of the adjuvant to the premix prepared asdescribed in Tables 2-2 and 2-3 below.

TABLE 2-2 (Composition 751-F) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba/MEA glyphosate premix 23.51 9.40% 1.20% ae potassium acetate(50%) 10.00 4.00% 2.00% water 216.48

TABLE 2-3 (Composition 210-F) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba/MEA glyphosate premix 23.48 9.39% 2.40% ae 1:1 wt/wt 50%potassium acetate/50% 10.04 4.00% 2.00% dipotassium phosphate Water216.51

TABLE 2-4 (Composition 210-E) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 32.2 32.12 12.75 1.35 MEA glyphosate (46.8%) 55.054.49 25.50 AGM 550 2.50 2.50 Agnique PG8107-G 5.1 5.00 SAG 1572 0.020.01 Ferric citrate (7.0% Fe) 0.33 0.31 0.02% 50% K acetate solution 5.75.7

The potassium acetate used in the formulations in Tables 2-5 throughTable 2-13 was prepared by adding the desired amount of glacial aceticacid to the desired amount of potassium hydroxide (45% w/w solution) inan ice bath without allowing the temperature of the solution to riseabove 60° C. The ratio indicated in the tables below is on a molarbasis. For example “50/50 AcOH/KOH” means a 1:1 M ratio of acetic acidto potassium hydroxide. The compositions in the tables below wereprepared by adding the desired amount of each ingredient and stirringfor about 20 minutes. Alternatively, the monocarboxylic acid salt can beprepared by adding the monocarboxylic acid to the solution containingthe herbicide(s) followed by addition of a neutralizing base.

The Fe dopant in Tables 2-8 through 2-13 (added to mitigate necrosis incertain crops) was prepared by mixing ferric sulfate and citric acid.

TABLE 2-5 (Composition 287-5) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (54.8% ae) 18.25 18.25 10.0 1.35 MEA glyphosate (46.9% ae) 42.7442.74 20.0 SAG 1572 0.01 0.01 Ferric Citrate (7.0% Fe) 0.31 0.31 0.0260/40 AcOH/KOH (38.7 AcOH) 6.98 6.98 2.70 water 31.72 31.72

TABLE 2-6 (Composition 287-6) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (54.8% ae) 17.34 17.34 9.50 1.35 MEA glyphosate (46.9% ae) 40.6040.60 19.00 SAG 1572 0.01 0.01 Ferric Citrate (7.0% Fe) 0.31 0.31 0.0260/40 AcOH/KOH (38.7 AcOH) 13.44 13.44 5.20 Water 28.30 28.30

TABLE 2-7 (Composition 512-1) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 31.61 31.61 12.55 1.35 MEA glyphosate (46.9% ae)53.63 53.63 25.10 AGM 550 2.50 2.50 AGNIQUE PG8107-G 5.00 5.00 SAG 15720.01 0.01 Ferric Citrate (7.0% Fe) 0.31 0.31 0.02 70/30 AcOH/KOH (38.7AcOH) 6.93 6.93

TABLE 2-8 (Composition 248-1) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 18.03 18.03 9.95 1.35 MEA glyphosate (46.8% ae) 45.5145.51 19.90 Ethoquad C12 75 DEG 3.49 3.49 SAG 1572 0.01 0.01 Fe Dopant(4.5% Fe) 0.49 0.49 0.02 60/40 AcOH/KOH (38.7 AcOH) 6.95 6.95 2.70 water28.49 28.49

TABLE 2-9 (Composition 248-2) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 18.08 18.08 9.95 1.35 MEA glyphosate (46.8% ae) 42.6242.62 19.90 Ethoquad C12 75 DEG 3.49 3.49 SAG 1572 0.02 0.02 Fe Dopant(4.5% Fe) 0.49 0.49 0.02 60/40 AcOH/KOH (38.7 AcOH) 10.86 10.86 4.20Water 24.61 24.61

TABLE 2-10 (Composition 248-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 17.91 17.91 9.90 1.35 MEA glyphosate (46.8% ae) 42.2842.28 19.80 Ethoquad C12 75 DEG 3.61 3.61 SAG 1572 0.02 0.02 Fe Dopant(4.5% Fe) 0.53 0.53 0.02 60/40 AcOH/KOH (38.7 AcOH) 13.95 13.95 5.40water 21.81 21.81

TABLE 2-11 (Composition 249-1) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 18.00 18.00 9.95 1.35 MEA glyphosate (46.8% ae) 42.5242.52 19.90 AGM 550 2.48 2.48 Agnique PG8107-G 1.95 1.95 SAG 1572 0.010.01 Fe Dopant (4.5% Fe) 0.60 0.60 0.02 60/40 AcOH/KOH (38.7 AcOH) 6.966.96 2.70 water 27.48 27.48

TABLE 2-12 (Composition 249-2) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 18.04 18.04 9.95 1.35 MEA glyphosate (46.8% ae) 42.5042.50 19.90 AGM 550 2.50 2.50 Agnique PG8107-G 2.00 2.00 SAG 1572 0.010.01 Fe Dopant (4.5% Fe) 0.49 0.49 0.02 60/40 AcOH/KOH (38.7 AcOH) 10.8310.83 4.20 water 23.59 23.59

TABLE 2-13 (Composition 249-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2%) 17.93 17.93 9.90 1.35 MEA glyphosate (46.8% ae) 42.3742.37 19.80 AGM 550 2.50 2.50 Agnique PG8107-G 1.97 1.97 SAG 1572 0.010.01 Fe Dopant (4.5% Fe) 0.49 0.49 0.02 60/40 AcOH/KOH (38.7 AcOH) 14.0014.00 5.40 water 20.79 20.79

TABLE 2-14 (Composition 530-2) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®125.63 25.13  9.90 ae 1.35 MEA glyphosate (46.8% ae) 211.54 42.31 19.80ae AGM 550 12.50 2.50 Agnique PG8107-G 10.00 2.00 SAG 1572 0.05 0.01 FeDopant (4.5% Fe) 1.94 0.39 0.02 65/35 AcOH/KOH (38.7 AcOH) 64.29 12.865.40 water 199.68

TABLE 2-15 (Composition 540-1) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®(39.4% a.e.) 124.37 24.87  9.80 ae 1.35 MEA glyphosate (46.8% ae) 209.4041.88 19.60 ae Ethoquad C12 75 DEG 17.50 3.50 65/35 AcOH/KOH (42.0%AcOH) 64.29 12.86 5.40 Fe Dopant (4.5% Fe) 1.94 0.39 0.0175 SAG 15720.05 0.01 water 82.45 16.49

TABLE 2-16 (Composition 540-4) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®(39.4% α.ε.) 123.10 24.62  9.70 ae 1.35 MEA glyphosate (46.8% ae) 207.2641.45 19.40 ae AGM 550 12.50 2.50 Agnique PG8107-G 10.00 2.00 SAG 15720.05 0.01 Fe Dopant (4.5% Fe) 1.94 0.39 0.0175 60/40 AcOH/KOH (38.7%AcOH) 69.77 13.95  5.40 Phosphate ester 5.00 1.000 water 70.38 14.08

Example 2-C: Liquid Concentrate Compositions (Dicamba)

TABLE 2-17 (Composition 871-5) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 73.43 73.43 29.00 potassium hydroxide 9.50 9.50acetic acid 5.91 5.91 water 11.16 11.16

TABLE 2-18 (Composition 871-4) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 73.49 73.49 29.03 potassium hydroxide 9.00 9.00acetic acid 5.93 5.93 water 11.58 11.58

TABLE 2-19 (Composition 871-12) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 72.53 72.53 28.65 potassium hydroxide 13.25 13.25acetic acid 7.65 7.65 water 6.57 6.57

TABLE 2-20 (Composition 761-2) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 72.47 72.47 28.63 potassium hydroxide 13.53 13.53acetic acid 9.72 9.72 water 4.28 4.28

TABLE 2-21 (Composition 771-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 64.11 64.11 25.32 potassium hydroxide 18.82 18.82acetic acid 13.52 13.52 water 3.55 3.55

TABLE 2-22 (Composition 871-2) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 73.43 73.43 29.00 potassium hydroxide 9.50 9.50acetic acid 5.91 5.91 PF 8000 Surfactant 1.00 1.00 water 10.16 10.16

TABLE 2-23 (Composition 871-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 73.07 73.07 28.86 potassium hydroxide 11.00 11.00acetic acid 5.88 5.88 PF 8000 Surfactant 1.00 1.00 water 9.05 9.05

TABLE 2-24 (Composition 871-6) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (CLARITY ®) 73.07 73.07 28.86 potassium hydroxide 5.88 5.88acetic acid 11.00 11.00 water 10.05 10.05

Example 2-D: Liquid Concentrate Compositions (Dicamba+Glyphosate)

TABLE 2-24 (Composition 540-1) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®(39.4% ae) 24.87 24.87 9.8 1.35 MEA glyphosate (45.6% ae) 42.98 42.9819.6 Ethoquad C12 75 DEG 3.5 3.5 SAG 1572 0.01 0.01 Ferric sulfate 0.140.14 Citric Acid 0.26 0.26 Acetic acid 5.32 5.32 potassium hydroxide(45% solution) 7.33 7.33 water 15.59 15.59

TABLE 2-25 (Composition 085-1) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®(39.4% ae) 24.87 24.87 9.8 1.35 MEA glyphosate (45.6% ae) 42.98 42.9819.6 Ethoquad C12 75 DEG 3.5 3.5 SAG 1572 0.01 0.01 Ferric sulfate 0.140.14 Citric acid 0.26 0.26 acetic acid 5.32 5.32 potassium hydroxide11.11 11.11 water 11.81 11.81

TABLE 2-26 (Composition 261) INGREDIENT T (g) WT % % ACTIVE CLARITY ®(39.4% ae) 24.87 24.87 9.8 1.35 MEA glyphosate (45.6% ae) 42.98 42.9819.6 AGM 550 2.5 2.5 Agnique PG 8107-G 2.0 2.0 SAG 1572 0.01 0.01 Ferricsulfate 0.14 0.14 Citric Acid 0.26 0.26 Acetic acid 5.32 5.32 potassiumhydroxide (45% soln) 7.33 7.33 water 14.59 14.59

TABLE 2-27 (Composition 567-2) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®(39.4% ae) 26.02 26.02 10.25 1.35 MEA glyphosate (45.6% ae) 44.96 44.9620.5 AGM 550 2.5 2.5 Agnique PG 8107-G 2.2 2.2 SAG 1572 0.01 0.01 Ferricsulfate 0.14 0.14 Citric Acid 0.26 0.26 Acetic acid 5.57 5.57 potassiumhydroxide (45% soln) 7.67 7.67 water 10.67 10.67

TABLE 2-28 (Composition 331-3) INGREDIENT WT (g) WT % % ACTIVE CLARITY ®(39.4% ae) 24.87 24.87 9.8 1.35 MEA glyphosate (45.6% ae) 42.98 42.9819.6 AGM 550 2.5 2.5 Agnique PG 8107-G 2.0 2.0 SAG 1572 0.01 0.01 Ferricsulfate 0.14 0.14 Citric Acid 0.26 0.26 Acetic acid 5.32 5.32 potassiumhydroxide (45% soln) 11.11 11.11 water 10.81 10.81

TABLE 2-29 (Composition 249-3) INGREDIENT WT (g) WT % % ACTIVE DGAdicamba (55.2% ae) 17.93 9.90 1.35 MEA glyphosate (46.8% ae) 42.31 19.80AGM 550 2.50 Agnique PG 8107-G 2.0 2.0 SAG 1572 0.01 0.01 Ferric sulfate0.19 0.19 Citric Acid 0.30 0.30 Potassium acetate (38.7% AcOH) 13.9513.95 5.40 water 20.81 20.81

Example 2-E: Dry Concentrate Compositions (Dicamba)

Dry granules having the compositions shown in Table 2-30 and Table 2-31were prepared. The sodium dicamba and the sodium acetate were mixedtogether in a blender. The PEG 8000, antifoam, and water were then addedto the blender and mixing continued. The amount of water added was anamount sufficient to generate a paste suitable for extrusion. The pastewas extruded under pressure through a 1 mm opening to obtain granules.The granules were extruded a total of three times to obtain granulesthat were not too dry. The final extruded granules were then dried in afluidized bed dryer at 70° C. to yield dry granules having an off-whitecolor.

TABLE 2-30 (Composition T2-30) INGREDIENT WT (g) WT % % ACTIVE Sodiumdicamba 85.00 85.00 68.0 Sodium acetate 10.00 10.00 PEG 8000 4.90 4.90Antifoam (Momentive, SAG 1572) 0.10 0.10

TABLE 2-31 (Composition T2-31) INGREDIENT WT (g) WT % % ACTIVE Sodiumdicamba 81.25 81.25 65.0 Sodium acetate 10.00 10.00 PEG 8000 4.90 4.90Antifoam (Momentive, SAG 1572) 0.10 0.10

Example 3: Measurement of Dicamba Volatility (Humidome)

Humidomes obtained from Hummert International (Part Nos 14-3850-2 forhumidomes and 11-3050-1 for 1020 flat tray) were modified by cutting a2.2 cm diameter hole on one end approximately 5 cm from the top to allowfor insertion of a glass air sampling tube (22 mm OD) containing apolyurethane foam (PUF) filter. The sampling tube was secured with aVITON o-ring on each side of the humidome wall. The air sampling tubeexternal to the humidome was fitted with tubing that was connected to avacuum manifold immediately prior to sampling.

The flat tray beneath the humidome was filled with 1 liter of sifted dryor wet 50/50 soil (50% Redi-Earth and 50% US 10 Field Soil) to a depthof about 1 cm. The flat tray bottom containing the dicamba formulationon soil was covered with the humidome lid and the lid was secured withclamps. The assembled humidomes were placed in a temperature andhumidity controlled environment and connected to a vacuum manifoldthrough the air sampling line. Air was drawn through the humidome andPUF at a rate of 2 liters per minute (LPM) for 24 hours at which pointthe air sampling was stopped. The humidomes were then removed from thecontrolled environment and the PUF filter was removed. The PUF filterwas extracted with 20 mL of methanol and the solution was analyzed fordicamba concentration using LC-MS methods known in the art.

To measure the dicamba concentration in the gas phase (air) thatvolatilized from the spray solutions, compositions were prepared tocontain 1.2% a.e. dicamba which is equivalent to an application rate of1.0 lb/A a.e. at 10 gallons per acre (GPA). Where glyphosate was addedor was part of the formulation, glyphosate was present at aconcentration of 2.4% a.e. or 2.0 lb/A a.e. Where 2,4-D was added or waspart of the formulation, 2,4-D was present at 2.4% ae or 2.0 lb/A ae at10 gallons per acre (GPA). The growth chambers were set at 35° C. and40% relative humidity (RH). For each composition four separate humidomeboxes were sprayed to have 4 replicate measurements for eachformulation. Tables 3-1 to 3-12 below provide the mean concentration ofdicamba in air for the tested formulations. Where concentrations ofdicamba were below the limits of detection, “nd” is indicated in thetables below.

Humidome Results:

TABLE 3-1 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 854-A 1.2% aeCLARITY ® 0.03 0.00 0.00 854-B 1.2% ae CLARITY ® + 0.44 0.11 0.06 2.4%ae POWERMAX ® 854-F 1.2% ae CLARITY ® + nd na na 2.4% ae POWERMAX ® + 2%potassium acetate 854-C 1.2% ae CLARITY ® + 0.06 0.01 0.01 2.4% aePOWERMAX ® + 2% dipotassium phosphate 854-D 1.2% ae CLARITY ® 0.47 0.130.06 2.4% ae POWERMAX ® + 2% potassium oxalate 854-E 1.2% ae CLARITY ®0.33 0.20 0.10 2.4% ae POWERMAX ® + 2% potassium citrate

TABLE 3-2 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 854-A 1.2% aeCLARITY ® 0.02 0.00 0.00 854-B 1.2% ae CLARITY ® + 0.49 0.16 0.08 2.4%ae POWERMAX ® 731-C 1.2% ae CLARITY ® + nd na na 2.4% ae POWERMAX ® + 2%potassium acetate 854-C 1.2% ae CLARITY ® + 0.04 0.01 0.01 2.4% aePOWERMAX ® + 2% dipotassium phosphate

TABLE 3-3 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 751-A 1.2% aeCLARITY ® 0.02 0.00 0.00 751-B 1.2% ae CLARITY ® + 1.04 0.50 0.25 2.4%ae POWERMAX ® 751-E 1.2% ae CLARITY ® + 6.13 0.55 0.32 2.4% aePOWERMAX ® + 1% AMS 751-C 1.2% ae CLARITY ® + nd na na 2.4% aePowerMAX + 2% potassium acetate 751-D 1.2% ae CLARITY ® + 3.63 0.77 0.382.4% ae POWERMAX ® + 2% potassium acetate + 1% ammonium sulfate

TABLE 3-4 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 210-A 1.2% aeCLARITY ® + 0.92 0.22 0.11 2.4% ae POWERMAX ® 210-B 1.2% ae Clarity + ndna na 2.4% ae POWERMAX ® + 2% potassium acetate 210-C 1.2% aeCLARITY ® + 0.16 0.02 0.01 2.4% ae POWERMAX ® + 2% potassium acetate +1% ammonium sulfate 210-D 1.2% ae CLARITY ® + 0.01 0.00 0.00 2.4% aePOWERMAX ® + 2% potassium acetate/ dipotassium phosphate

TABLE 3-5 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 870-A 2.4% aeDURANGO ® 0.10 0.03 0.01 DMA ® + 2.4% 2,4-D amine 870-B 2.4% aeDURANGO ® 0.01 0.00 0.00 DMA ® + 2.4% 2,4-D amine + 2% potassium acetate870-D 2.4% ae IPA glyphosate + 0.09 0.03 0.01 2.4% ae 2,4-D amine 870-C2.4% ae IPA glyphosate + 0.01 0.01 0.00 2.4% ae 2,4-D amine + 2%potassium acetate

TABLE 3-6 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 563-2 1.2% aeBANVEL ® + 1.92 0.31 0.15 2.4% POWERMAX ® 563-5 1.2% ae BANVEL ® + 0.020.01 0.00 2.4% POWERMAX ® + 2% potassium acetate 563-3 1.2% aeCLARITY ® + 0.49 0.13 0.06 2.4% ae PowerMAX 563-6 1.2% ae CLARITY ® +0.01 0.01 0.00 2.4% ae POWERMAX ® + 2% potassium acetate 563-1 1.2% aeMEA dicamba + 1.04 0.24 0.12 2.4% ae POWERMAX ® 563-4 1.2% ae MEAdicamba + 0.01 0.00 0.00 2.4% ae POWERMAX ® + 2% potassium acetate

TABLE 3-7 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 751-F 1.2% aeDGA dicamba/MEA nd na na glyphosate premix + 2% potassium acetate 210-E1.2% ae DGA dicamba/MEA 0.07 0.01 0.00 glyphosate/ 0.54% potassiumacetate premix 210-F 1.2% DGA dicamba/MEA 0.01 0.00 0.00 glyphosatepremix + 2% potassium acetate/dipotassium phosphate

TABLE 3-8 DICAMBA STD STD ID COMPOSITION (ng/L) DEV ERROR 893-A 1.2% aeCLARITY ® + 0.83 0.10 0.05 2.4% POWERMAX ® 893-B 1.2% ae CLARITY ® +0.003 0.00 0.00 2.4% POWERMAX ® + 2% potassium acetate 893-C 1.2% aeCLARITY ® + 0.007 0.00 0.00 2.4% POWERMAX ® + 2% potassium benzoate893-D 1.2% ae CLARITY ® + 0.003 0.00 0.00 2.4% POWERMAX ® + 2% potassiumformate 893-E 1.2% ae CLARITY ® + 0.001 0.00 0.00 2.4% POWERMAX ® + 2%sodium acetate

TABLE 3-9 MOLAR MOLAR RATIO RATIO CARBOXYLIC CARBOXYLIC DICAMBA STD STDID COMPOSITION ACID:DICAMBA ACID:KOH (ng/L) DEV ERR 836-1 1.2% aeCLARITY ® + NA NA 1.139 0.34 0.17 2.4% POWERMAX ® 836-6 1.2% aeCLARITY ® + NA NA 0.029 0.01 0.00 2.4% POWERMAX ® + potassium hydroxide836-3 1.2% ae CLARITY ® + 2:1 1:1 0.011 0.01 0.00 2.4% POWERMAX ® +propionic acid + potassium hydroxide 836-5 1.2% ae CLARITY ® + 2:1 1:10.012 0.00 0.00 2.4% POWERMAX ® + formic acid + potassium hydroxide836-2 1.2% ae CLARITY ® + 2:1 1:2 0.064 0.01 0.01 2.4% POWERMAX ® +succinic acid + potassium hydroxide 836-4 1.2% ae CLARITY ® + 2:1 1:10.014 0.01 0.00 2.4% POWERMAX ® + acetic acid + potassium hydroxide

TABLE 3-10 DICAMBA STD STD ID COMPOSITION* (ng/L) DEV ERROR 321-1 1.2%ae CLARITY ® 0.016 0.005 0.003 321-2 1.2% Composition 871-2 0.004 0.0010.001 321-3 1.2% Composition 871-3 0.005 0.003 0.002 321-4 1.2%Composition 871-4 0.003 0.000 0.000 321-5 1.2% Composition 871-5 0.0030.000 0.000 321-6 1.2% Composition 871-6 0.003 0.001 0.000 *Testformulation was prepared by diluting referenced Composition with anamount of water sufficient to provide a test formulation containing 1.2%a.e. dicamba.

TABLE 3-11 DICAMBA STD STD ID COMPOSITION* (ng/L) DEV ERROR 891-1 1.2%ae CLARITY ® 0.367 0.110 0.039 917-2 1.2% ae CLARITY ® + 0.015 0.0040.001 2.4% ae POWERMAX ® 917-3 1.2% ae Composition 261 0.006 0.002 0.000*Test formulation was prepared by diluting referenced Composition withan amount of water sufficient to provide a test formulation containing1.2% a.e. dicamba.

TABLE 3-12 DICAMBA STD STD ID COMPOSITION* (ng/L) DEV ERROR 364-1 1.2%ae CLARITY ® 0.049 0.018 0.009 364-2 1.2% ae Clarity + 1.938 0.020 0.0123.36% v/v Liberty 364-3 1.2% ae Clarity + 0.031 0.013 0.007 3.36% v/vLiberty + 3% v/v dipotassium phosphate 364-4 1.2% ae Composition 871-50.002 0.003 0.001 364-5 1.2% ae Composition 871-5 + 0.191 0.033 0.0193.36% v/v Liberty 364-6 1.2% ae Composition 871-5 + 0.013 0.002 0.0013.36% v/v Liberty + 3% dipotassium phosphate *Test formulation wasprepared by diluting referenced Composition with an amount of watersufficient to provide a test formulation containing 1.2% a.e. dicamba.

TABLE 3-12 STD DICAMBA STD ER- ID COMPOSITION* (ng/L) DEV ROR 268-1 1.2%ae CLARITY ® + 4.76 0.96 0.48 2.4% ae ROUNDUP ® ENERGY 268-2 1.2% aeCLARITY ® + 1.11 0.47 0.23 2.4% ae ROUNDUP ® ENERGY + 3% dipotassiumphosphsate 268-3 1.2% ae CLARITY ® + 0.17 0.13 0.06 2.4% ae ROUNDUP ®ENERGY + 2% potassium acetate 268-4 1.2% ae CLARITY ® + 0.00 0.00 0.002.4% ae ROUNDUP ® ENERGY + 4% potassium acetate 268-5 1.2% aeCLARITY ® + 0.01 0.01 0.00 2.4% ae ROUNDUP ® ENERGY + 2% potassiumacetate + 3% dipotassium phosphate 268-6 1.2% ae CLARITY + 1.55 0.520.26 2.4% ae PowerMAX *ROUNDUP ® ENERGY is the glyphosate ammonium salt,sold as water soluble granules in Europe.

The results reported above for the di- and tri-carboxylic acids tested(oxalic acid, citric acid, and succinic acid) indicate that those acidsdid not reduce dicamba volatility. In addition, malic acid was testedand likewise did not reduce dicamba volatility.

Example 4: Measurement of Dicamba Volatility (Plant Response)

Herbicidal compositions were sprayed onto eight 90 mm diameter glassPetri dishes. The eight Petri dishes were placed immediately on aplastic tray along with two Roundup Ready soybean plants at V1-V1.5development stage as indicators. The plastic trays were then coveredwith plastic domes, sealed with clamps around edges, and placed in thegrowth chamber, at a set temperature and relative humidity (85° F. day(16 h light), 70° F. night (8 h dark) and 40% RH) for 24 hours. After 24hours, the plants were removed from the domes and transferred to agreenhouse. The indicator plants were evaluated for visual symptomstypically at 5, 7 and 14 days after treatment.

Plant response results for compositions containing dicamba are listed inTables 4-1, 4-2, and 4.3:

TABLE 4-1 ID COMPOSITION % INJURY (7 DAT) 889-A 1.2% ae DGA dicamba 15%889-D 1.2% ae DGA dicamba + 0 2% potassium acetate

TABLE 4-2 % INJURY % INJURY ID COMPOSITION* (7 DAT) (14 DAT) 321-1 1.2%ae CLARITY ® 10.00 23.33 321-2 1.2% Composition 871-2 0.00 5.13 321-31.2% Composition 871-3 0.63 8.50 321-4 1.2% Composition 871-4 4.13 15.38321-5 1.2% Composition 871-5 2.63 10.75 321-6 1.2% Composition 871-65.38 15.38 *Test formulation was prepared by diluting referencedComposition with an amount of water sufficient to provide a testformulation containing 1.2% a.e. dicamba.

TABLE 4-3 % INJURY % INJURY ID COMPOSITION* (7 DAT) (14 DAT) 891-1 1.2%ae CLARITY ® 6.44 25.31 917-2 1.2% ae CLARITY ® + 12.50 44.38 2.4% aePOWERMAX ® 917-3 1.2% ae Composition 261 3.25 9.75 *Test formulation wasprepared by diluting referenced Composition with an amount of watersufficient to provide a test formulation containing 1.2% a.e. dicamba.

Example 5: Measurement of Herbicidal Effectiveness

The herbicidal effectiveness of the compositions of the presentinvention can be assessed through conventional greenhouse tests and/orfield tests. Herbicidal effectiveness can be measured as a percentage“inhibition” following a standard procedure in the art which reflects avisual assessment of plant mortality and growth reduction by comparisonwith untreated plants, made by technicians specially trained to make andrecord such observations. In all cases, a single technician makes allassessments of percent inhibition within any one experiment or trial.Such measurements are relied upon and regularly reported by MonsantoTechnology LLC in the course of its herbicide business.

The selection of application rates that are biologically effective for aspecific auxin herbicide is within the skill of the ordinaryagricultural scientist. Those of skill in the art will likewiserecognize that individual plant conditions, weather and growingconditions, as well as the specific exogenous chemical and formulationthereof selected, will affect the weed efficacy and associated cropinjury achieved in practicing this invention. Useful application ratesfor the auxin herbicides employed can depend upon all of the aboveconditions. With respect to the use of the method of this invention,much information is known about appropriate auxin application rates, anda weed control practitioner can select auxin application rates that areherbicidally effective on particular species at particular growth stagesin particular environmental conditions.

Effectiveness in greenhouse tests, usually at exogenous chemical rateslower than those normally effective in the field, is a proven indicatorof consistency of field performance at normal use rates.

The compositions of the present invention can be applied to plants byspraying, using any conventional means for spraying liquids, such asspray nozzles, atomizers, or the like. Compositions of the presentinvention can be used in precision farming techniques, in whichapparatus is employed to vary the amount of exogenous chemical appliedto different parts of a field, depending on variables such as theparticular plant species present, soil composition, and the like. In oneembodiment of such techniques, a global positioning system operated withthe spraying apparatus can be used to apply the desired amount of thecomposition to different parts of a field.

The composition, at the time of application to plants, is preferablydilute enough to be readily sprayed using standard agricultural sprayequipment. Preferred application rates for the present invention varydepending upon a number of factors, including the type and concentrationof active ingredient and the plant species involved. Useful rates forapplying an aqueous composition to a field of foliage can range fromabout 25 to about 1,000 liters per hectare (1/ha) by spray application.The preferred application rates for aqueous solutions are in the rangefrom about 50 to about 300 I/ha.

Many exogenous chemicals (including auxin herbicides) must be taken upby living tissues of the plant and translocated within the plant inorder to produce the desired biological (e.g., herbicidal) effect. Thus,it is important that an herbicidal formulation not be applied in such amanner as to excessively injure and interrupt the normal functioning ofthe local tissue of the plant so quickly that translocation is reduced.However, some limited degree of local injury can be insignificant, oreven beneficial, in its impact on the biological effectiveness ofcertain exogenous chemicals.

Results obtained with application of the composition to green foxtail(SETVI), velvetleaf (ABUTH), and hemp sesbania (SEBEX) are shown inTables 5-1, 5-2, and 5-3, respectively. In each case, application rateswere 280 g ae/ha for dicamba and 560 g ae/ha for glyphosate, and thereported result is an average of the results obtained from six separateapplications.

TABLE 5-2 Green Foxtail (SETVI) Composition AVG % CONTROL ROUNDUPPOWERMAX ® + CLARITY ® 99.7 Composition 249-3 99.7

TABLE 5-2 Velvetleaf (ABUTH) Composition AVG % CONTROL ROUNDUPPOWERMAX ® + CLARITY ® 90.8 Composition 249-3 86.7

TABLE 5-2 Hemp Sesbania (SEBEX) Composition AVG % CONTROL ROUNDUPPOWERMAX ® + CLARITY ® 99.2 Composition 249-3 100

Example 6: Herbicidal Efficacy on ABUTH (Velvetleaf) and ELEIN(Gooseqrass)

The herbicidal tank mix compositions listed in the tables below wereprepared using CLARITY® (DGA dicamba from BASF) and ROUNDUP POWERMAX®(potassium glyphosate from Monsanto) by successively adding eachspecified herbicide to water and mixing. The tank mixtures containingpotassium acetate were prepared as described in Example 1.

Weed seeds were planted in 3.5 in square plastic pots filled withRedi-earth (Sun Gro, Bellevue, Wash.) containing 100 g/cu ft Osmocote14-14-14 slow release fertilizer. Ten to fifteen weed seeds were plantedabout one-half inch deep and loosely covered with Redi-Earth pottingmedia. The pots were placed in a controlled environment equipped withsub-irrigation. Growth conditions were 27° C. day and 21° C. night withfourteen hours of supplemental light (approximately 600 microeinsteins).After germination and emergence from the potting media, the plants werethinned to achieve one plant per pot. Pots that contained plants thatwere similar in appearance, size, and vigor were selected for treatment.Typically, the plants were four to eight inches tall at the time ofherbicide treatment. Compositions were applied to the plants with atrack sprayer generally using a Teejet 9501E flat fan nozzle or similarnozzle with air pressure set at a minimum of 24 pounds per square inch.The spray nozzle was 16 inches above the top of the plants and a sprayvolume rate of approximately 10 gallons per acre (93 L per hectare) wasapplied. Each composition was applied at three application rates andherbicide injury rating was made 21 days post treatment.

TABLE 6-1 Herbicidal Efficacy of Tank Mixtures Containing POWERMAX ® andDGA dicamba/potassium acetate on ABUTH (velvetleaf) and ELEIN(goosegrass) % CONTROL AMT (21 DAT) COMPOSITION (% ae) RATE ABUTH ELEINPOWERMAX ® 39.8 140 ae g/ha 0.0 23.3 280 ae g/ha 52.5 85.0 560 ae g/ha74.2 93.8 CLARITY ® 40  70 ae g/ha 10.0 0.0 140 ae g/ha 18.3 10.0 280 aeg/ha 36.7 10.0 503-1 31.0  70 ae g/ha 10.8 0.0 503-1 31.0 140 ae g/ha19.2 0.0 503-1 31.0 280 ae g/ha 33.3 0.0 503-3 31.0  70 ae g/ha 10.0 8.3503-3 31.0 140 ae g/ha 17.5 11.7 503-3 31.0 280 ae g/ha 35.0 7.5 295-331.0  70 ae g/ha 13.3 8.3 295-3 31.0 140 ae g/ha 20.0 11.7 295-3 31.0280 ae g/ha 36.7 7.5 295-6 31.0  70 ae g/ha 12.5 0.0 295-6 31.0 140 aeg/ha 21.7 0.0 295-6 31.0 280 ae g/ha 43.3 3.3 POWERMAX ® 39.8 140 aeg/ha 14.2 38.3 CLARITY ® 40  70 ae g/ha POWERMAX ® 39.8 280 ae g/ha 46.785.0 CLARITY ® 40 140 ae g/ha POWERMAX ® 39.8% ae 560 ae g/ha 80.8 95.0CLARITY ®   40% ae 280 ae g/ha POWERMAX ® 39.8% ae 140 ae g/ha 11.7 39.2503-1 31.0% ae  70 ae g/ha POWERMAX ® 39.8% ae 280 ae g/ha 62.5 81.7503-1 31.0% ae 140 ae g/ha POWERMAX ® 39.8% ae 560 ae g/ha 82.5 94.2503-1 31.0% ae 280 ae g/ha POWERMAX ® 39.8% ae 140 ae g/ha 15.0 35.0503-3 31.0% ae  70 ae g/ha POWERMAX ® 39.8% ae 280 ae g/ha 49.2 83.3503-3 31.0% ae 140 ae g/ha POWERMAX ® 39.8% ae 560 ae g/ha 83.3 93.3503-3 31.0% ae 280 ae g/ha POWERMAX ® 39.8% ae 140 ae g/ha 15.8 26.7295-3 31.0% ae  70 ae g/ha POWERMAX ® 39.8% ae 280 ae g/ha 54.2 82.5295-3 31.0% ae 140 ae g/ha POWERMAX ® 39.8% ae 560 ae g/ha 83.3 90.0295-3 31.0% ae 280 ae g/ha POWERMAX ® 39.8% ae 140 ae g/ha 17.5 42.5295-6 31.0% ae  70 ae g/ha POWERMAX ® 39.8% ae 280 ae g/ha 55.0 80.0295-6 31.0% ae 140 ae g/ha POWERMAX ® 39.8% ae 560 ae g/ha 85.8 85.0295-6 31.0% ae 280 ae g/ha UNTREATED 0 0 0.0 1.0 CHECK

Herbicidal premix compositions listed in the tables below were preparedas previously described in Example 2.

TABLE 6-2 Herbicidal efficacy of premix composition containingglyphosate, dicamba and potassium acetate on ABUTH (velvetleaf) andELEIN (goosegrass) % CONTROL (21 DAT) COMPOSITION ABUTH ELEIN RATEPOWERMAX ®    140 ae g/ha 21.7 78.3    280 ae g/ha 71.7 95.0    560 aeg/ha 84.2 99.0 CLARITY ®    70 ae g/ha 20.0 0.0    140 ae g/ha 36.7 0.0   280 ae g/ha 60.8 0.0 POWERMAX ®    140 ae g/ha 26.7 81.7 CLARITY ®   70 ae g/ha POWERMAX ®    280 ae g/ha 59.2 90.0 CLARITY ®    140 aeg/ha POWERMAX ®    560 ae g/ha 85.8 92.5 CLARITY ®    280 ae g/ha RATEGLY/DICAMBA 287-5  140/70 ae g/ha 20.0 0.0 280/140 ae g/ha 51.7 10.0560/280 ae g/ha 71.7 68.3 287-6  140/70 ae g/ha 18.3 0.0 280/140 ae g/ha50.0 10.0 560/280 ae g/ha 73.3 39.2 512-1  140/70 ae g/ha 22.5 84.2280/140 ae g/ha 64.2 93.3 560/280 ae g/ha 92.7 97.2 248-1  140/70 aeg/ha 32.5 78.3 280/140 ae g/ha 63.3 92.2 560/280 ae g/ha 85.5 95.0 248-2 140/70 ae g/ha 38.3 78.3 280/140 ae g/ha 57.5 93.3 560/280 ae g/ha 85.895.0 248-3  140/70 ae g/ha 30.0 80.8 280/140 ae g/ha 51.7 90.8 560/280ae g/ha 84.7 96.5 249-1  140/70 ae g/ha 33.3 81.7 280/140 ae g/ha 59.290.0 560/280 ae g/ha 92.2 98.0 249-2  140/70 ae g/ha 30.0 80.8 280/140ae g/ha 58.3 90.8 560/280 ae g/ha 89.7 97.3 249-3  140/70 ae g/ha 30.886.7 280/140 ae g/ha 63.3 91.7 560/280 ae g/ha 86.7 98.2 UNTREATED 0 0.00.0 CHECK

This written description uses examples to disclose the invention,including the best mode, and also to enable any person skilled in theart to practice the invention, including making and using any devices orsystems and performing any incorporated methods. The patentable scope ofthe invention is defined by the claims, and may include other examplesthat occur to those skilled in the art. Such other examples are intendedto be within the scope of the claims if they have structural elementsthat do not differ from the literal language of the claims, or if theyinclude equivalent structural elements with insubstantial differencesfrom the literal languages of the claims.

What is claimed is:
 1. A herbicidal composition concentrate comprising:dicamba, or an agriculturally acceptable salt or ester thereof; and apotassium or sodium monocarboxylate of a monocarboxylic acid; wherein:the concentrate comprises an amount of the potassium or sodiummonocarboxylate sufficient to reduce the concentration of volatilizeddicamba in the vapor phase surrounding a diluted version of theconcentrate relative to the concentration of volatilized dicamba in thevapor phase surrounding an otherwise identical diluted version of theconcentrate lacking the potassium or sodium monocarboxylate.
 2. Theherbicidal composition concentrate of claim 1, wherein the concentratecomprises an agriculturally acceptable salt of dicamba selected from thegroup consisting of N,N-bis-[aminopropyl]methylamine, monoethanolamine,dimethylamine, isopropylamine, diglycolamine, potassium, and sodiumsalts, and combinations thereof.
 3. The herbicidal compositionconcentrate of claim 1, wherein the concentrate comprises thediglycolamine salt of dicamba.
 4. The herbicidal composition concentrateof claim 1, wherein the monocarboxylic acid is selected from the groupconsisting of formic acid, acetic acid, propionic acid, and benzoicacid.
 5. The herbicidal composition concentrate of claim 1, wherein theconcentrate comprises the potassium or sodium monocarboxylate salt, inwhole or in part, in dissociated form, the monocarboxylate salt selectedfrom the group consisting of formate salts, acetate salts, propionatesalts, and benzoate salts of the monocarboxylic acid.
 6. The herbicidalcomposition concentrate of claim 1, wherein the concentrate comprisesacetic acid, or an agriculturally acceptable salt thereof.
 7. Theherbicidal composition concentrate of claim 1, wherein the concentratecomprises an additive selected from the group consisting of surfactants,drift reduction agents, safeners, solubility enhancing agents,thickening agents, flow enhancers, foam-moderating agents, freezeprotectants, UV protectants, preservatives, antimicrobials, and/or otheradditives that are necessary or desirable to improve the performance,crop safety, or handling of the composition.
 8. The herbicidalcomposition concentrate of claim 1, wherein the concentrate comprisesless than about 10 ppm of ammonium sulfate.
 9. The herbicidalcomposition concentrate of claim 1, wherein the concentrate containsdicamba at a total loading of from about 120 to about 600 g acidequivalent (a.e.)/L.
 10. The herbicidal composition concentrate of claim1, wherein the concentrate contains dicamba at a total loading of fromabout 300 g a.e./L to about 600 g a.e./L.
 11. The herbicidal compositionconcentrate of claim 1, wherein the concentrate contains dicamba at atotal loading of from about 350 g a.e./L to about 600 g a.e./L.
 12. Theherbicidal composition concentrate of claim 1, wherein the concentratecontains dicamba at a total loading of from about 400 g a.e./L to about600 g a.e./L.
 13. The herbicidal composition concentrate of claim 1,wherein the concentrate contains dicamba at a total loading of fromabout 450 g a.e./L to about 600 g a.e./L.
 14. The herbicidal compositionconcentrate of claim 1, wherein the concentrate contains dicamba at atotal loading of from about 500 g a.e./L to about 600 g a.e./L.
 15. Theherbicidal composition concentrate of claim 1, wherein the compositionis a liquid concentrate containing a total amount (acid equivalentweight) of dicamba from about 5% to about 75% by weight of theconcentrate.
 16. The herbicidal composition concentrate of claim 1,wherein the composition is a liquid concentrate containing a totalamount (acid equivalent weight) of dicamba from about 25% to about 35%by weight of the concentrate.
 17. The herbicidal composition concentrateof claim 1, wherein the composition is a dry concentrate containing atotal amount (acid equivalent weight) of dicamba from about 40% to about90% by weight of the concentrate.
 18. The herbicidal compositionconcentrate of claim 1, wherein the molar ratio of dicamba to thepotassium or sodium monocarboxylate, is from about 1:10 to about 10:1.19. The herbicidal composition concentrate of claim 1, wherein the molarratio of dicamba to the potassium or sodium monocarboxylate, is fromabout 2:1 to about 1:2.
 20. The herbicidal composition concentrate ofclaim 1, wherein the concentration of the potassium or sodiummonocarboxylate, is from about 1 gram (acid equivalent weight)/L toabout 250 grams (acid equivalent weight)/L.
 21. The herbicidalcomposition concentrate of claim 1, wherein the concentrate comprises anamount (acid equivalent weight) of the potassium or sodiummonocarboxylate, of from about 1% to about 20% by weight of theconcentrate.
 22. The herbicidal composition concentrate of claim 1,wherein the concentrate comprises an amount (acid equivalent weight) ofthe potassium or sodium monocarboxylate, of from about 2% to about 15%by weight of the concentrate.
 23. The herbicidal composition concentrateof claim 1, wherein the concentrate is a liquid concentrate andcomprises an amount (acid equivalent weight) of the monocarboxylate, offrom about 2% to about 10% by weight of the concentrate.
 24. Theherbicidal composition concentrate of claim 1, wherein the concentrateis a dry concentrate and comprises an amount (acid equivalent weight) ofthe monocarboxylate, of from about 5% to about 15% by weight of theconcentrate.
 25. The herbicidal composition concentrate of claim 1,wherein the composition comprises: acetic acid, or an agriculturallyacceptable salt thereof; wherein the molar ratio of acetic acid, oragriculturally acceptable salt thereof, to dicamba, or agriculturallyacceptable salt or ester thereof, is from about 1:10 to about 10:1;and/or wherein the acid equivalent weight ratio of acetic acid, oragriculturally acceptable salt thereof, to dicamba, or agriculturallyacceptable salt or ester thereof, is from about 1:10 to about 5:1;and/or wherein the concentrate contains an amount (acid equivalentweight) of the acetic acid, or agriculturally acceptable salt thereof,from about 0.25% to about 25% by weight of the concentrate; and/orwherein the concentration of the acetic acid, or agriculturallyacceptable salt thereof, is from about 1 gram (acid equivalent weight)/Lto about 250 grams (acid equivalent weight)/L; and/or wherein theconcentration of dicamba, or an agriculturally acceptable salt or esterthereof, is from about 120 grams (acid equivalent weight)/L to about 600grams (acid equivalent weight)/L.
 26. The herbicidal compositionconcentrate of claim 1, wherein the composition comprises: acetic acid,or an agriculturally acceptable salt thereof; wherein the concentrationof dicamba, or an agriculturally acceptable salt or ester thereof, isfrom about 120 grams (acid equivalent weight)/L to about 600 grams (acidequivalent weight)/L; and wherein the acid equivalent weight ratio ofacetic acid, or agriculturally acceptable salt thereof, to dicamba, oragriculturally acceptable salt or ester thereof, is from about 1:10 toabout 5:1.
 27. The herbicidal composition concentrate of claim 1,wherein the composition comprises: acetic acid, or an agriculturallyacceptable salt thereof; and wherein: the concentrate contains an amount(acid equivalent weight) of the acetic acid, or agriculturallyacceptable salt thereof, from about 1% to about 25% by weight of theconcentrate; and the concentrate contains an amount (acid equivalentweight) of dicamba, or an agriculturally acceptable salt or esterthereof, from about 10% to about 60% by weight of the concentrate. 28.The herbicidal composition concentrate of claim 1, wherein thecomposition comprises: acetic acid, or an agriculturally acceptable saltthereof; and wherein: the concentrate contains an amount (acidequivalent weight) of the acetic acid, or agriculturally acceptable saltthereof, from about 2% to about 20% by weight of the concentrate; andthe concentrate contains an amount (acid equivalent weight) of dicamba,or an agriculturally acceptable salt or ester thereof, from about 15% toabout 50% by weight of the concentrate.
 29. The herbicidal compositionconcentrate of claim 1, wherein the composition comprises: acetic acid,or an agriculturally acceptable salt thereof; and wherein: theconcentrate contains an amount (acid equivalent weight) of the aceticacid, or agriculturally acceptable salt thereof, from about 3% to about15% by weight of the concentrate; and the concentrate contains an amount(acid equivalent weight) of dicamba, or an agriculturally acceptablesalt or ester thereof, from about 20% to about 40% by weight of theconcentrate.
 30. The herbicidal composition concentrate of claim 1,wherein the composition comprises: acetic acid, or an agriculturallyacceptable salt thereof; and wherein: the concentrate contains an amount(acid equivalent weight) of the acetic acid, or agriculturallyacceptable salt thereof, from about 3% to about 10% by weight of theconcentrate; and the concentrate contains an amount (acid equivalentweight) of dicamba, or an agriculturally acceptable salt or esterthereof, from about 25% to about 35% by weight of the concentrate. 31.The herbicidal composition concentrate of claim 1, wherein theconcentrate is a dry concentrate comprising: acetic acid, or anagriculturally acceptable salt thereof; and wherein: the concentratecontains an amount (acid equivalent weight) of the acetic acid, oragriculturally acceptable salt thereof, from about 1% to about 40% byweight of the concentrate; the concentrate contains an amount (acidequivalent weight) of dicamba, or an agriculturally acceptable salt orester thereof, from about 40% to about 90% by weight of the concentrate;and wherein the sum of the acetic acid weight percent and the dicambaweight percent is less than or equal to 100%.
 32. The herbicidalcomposition concentrate of claim 1, wherein the concentrate is a dryconcentrate comprising: acetic acid, or an agriculturally acceptablesalt thereof; wherein: the concentrate contains an amount (acidequivalent weight) of the acetic acid, or agriculturally acceptable saltthereof, from about 3% to about 30% by weight of the concentrate; andthe concentrate contains an amount (acid equivalent weight) of dicamba,or an agriculturally acceptable salt or ester thereof, from about 50% toabout 80% by weight of the concentrate; and wherein the sum of theacetic acid weight percent and the dicamba weight percent is less thanor equal to 100%.
 33. The herbicidal composition concentrate of claim 1,wherein the concentrate is a dry concentrate comprising: acetic acid, oran agriculturally acceptable salt thereof; and wherein: the concentratecontains an amount (acid equivalent weight) of the acetic acid, oragriculturally acceptable salt thereof, from about 5% to about 20% byweight of the concentrate; and the concentrate contains an amount (acidequivalent weight) of dicamba, or an agriculturally acceptable salt orester thereof, from about 60% to about 75% by weight of the concentrate.34. A herbicidal composition concentrate comprising: (a) dicamba, or anagriculturally acceptable salt or ester thereof; (b) at least onemonocarboxylic acid; and (c) a neutralizing base, wherein theneutralizing base is an alkali metal hydroxide selected from potassiumhydroxide, sodium hydroxide, or a mixture thereof, wherein: theconcentrate comprises an amount of the monocarboxylic acid andneutralizing base sufficient to reduce the concentration of volatilizeddicamba in the vapor phase surrounding a diluted version of theconcentrate relative to the concentration of volatilized dicamba in thevapor phase surrounding an otherwise identical diluted version of theconcentrate lacking the monocarboxylic acid, and neutralizing base. 35.A herbicidal composition comprising: (a) dicamba or an agriculturallyacceptable salt or ester thereof; (b) at least one monocarboxylic acid,or a monocarboxylate thereof; (c) a neutralizing base, wherein theneutralizing base is an alkali metal hydroxide selected from potassiumhydroxide, sodium hydroxide, or a mixture thereof; and (d) water;wherein: the composition comprises an amount of the monocarboxylic acidand neutralizing base, or an amount of the monocarboxylate, sufficientto reduce the concentration of volatilized dicamba in the vapor phasesurrounding the composition relative to the concentration of volatilizeddicamba in the vapor phase surrounding an otherwise identicalcomposition lacking the monocarboxylic acid and neutralizing base, ormonocarboxylate.
 36. The herbicidal composition of claim 35, wherein theherbicidal composition is prepared by a process comprising: mixing thedicamba, or agriculturally acceptable salt or ester thereof, themonocarboxylic acid, and a neutralizing base comprising an alkali metalhydroxide selected from potassium hydroxide, sodium hydroxide, or amixture thereof, thereby forming a liquid concentrate comprising thedicamba, or agriculturally salt or ester thereof, and themonocarboxylate.
 37. The herbicidal composition of claim 35, wherein theherbicidal composition is prepared by a process comprising: mixing thedicamba, or agriculturally acceptable salt or ester thereof, with themonocarboxylate, thereby forming a liquid concentrate comprising thedicamba, or agriculturally acceptable salt or ester thereof, and themonocarboxylate.
 38. The herbicidal composition of claim 35, wherein:the molar ratio of monocarboxylic acid, or monocarboxylate thereof, todicamba, or an agriculturally acceptable salt or ester thereof, is fromabout 1:10 to about 10:1; and/or the acid equivalent weight ratio ofmonocarboxylic acid, or monocarboxylate thereof, to dicamba, or anagriculturally acceptable salt or ester thereof, is from about 1:10 toabout 5:1; and/or the composition comprises an amount (acid equivalentweight) of the monocarboxylic acid, or monocarboxylate thereof, fromabout 0.01% to about 25% by weight of the composition; and/or theconcentration of the monocarboxylic acid, or monocarboxylate thereof, isfrom about 1 gram (acid equivalent weight)/L to about 250 grams (acidequivalent weight)/L.
 39. The herbicidal composition of claim 35,wherein the concentration of dicamba, or an agriculturally acceptablesalt or ester thereof, is from about 0.1 grams (acid equivalentweight)/L to about 50 grams (acid equivalent weight)/L.
 40. Theherbicidal composition of claim 35, wherein the concentration ofdicamba, or an agriculturally acceptable salt or ester thereof, is fromabout 10 grams (acid equivalent weight)/L to about 50 grams (acidequivalent weight)/L.
 41. The herbicidal composition of claim 35,wherein the composition comprises an amount (acid equivalent weight) ofthe monocarboxylic acid, or monocarboxylate thereof, from about 0.05% toabout 5% by weight of the composition.
 42. The herbicidal composition ofclaim 35, wherein the neutralizing base is potassium hydroxide.
 43. Theherbicidal composition of claim 35, wherein the neutralizing base issodium hydroxide.
 44. The herbicidal composition of claim 35, comprisingthe neutralizing base and monocarboxylic acid at a molar ratio of about50:50 (1:1) or about 60:40 (1.5:1).
 45. The herbicidal composition ofclaim 35, wherein the composition has a pH equal to or higher than theacid dissociation constant (pKa) of the monocarboxylic acid present inthe composition.